a：Benzyl butyrate (250 μL, 1.4 mmol) and aldehyde (1.4 mmol) were dissolved in 5 mL MeOH, 25 mL saturated NaHSO3(aq) added, shaken for approximately 30 s, diluted with 25 mL H2O, and extracted with 25 mL 10% EA/hexanes. b：DMF instead of MeOH used. Organic layer washed two times with 15 mL water. c：Required filtration to remove solid bisulfite adduct.
利用DMF作为水溶性促溶溶剂，验证脂肪醛的纯化效果。
a：Aldehyde (1.4 mmol) and benzyl butyrate (250 μL, 1.4 mmol) were dissolved in 10 mL DMF, 25 mL saturated NaHSO3(aq) added, shaken for approximately 30 s, diluted with 25 mL H2O, and extracted with 25 mL hexanes. The aqueous layer was extracted once with hexanes and the combined organics were washed three times with water to remove DMF (25 mL, 10 mL, 5 mL). b：Required filtration to remove solid bisulfite adduct. c：Pentane used in place of hexanes. d：10% EA/hexanes used in place of hexanes. e：MeOH used in place of DMF. f：CHCl3 used in place of hexanes.
另外一些高活性的酮，也可以通过此方法除去。
Standard work-up procedure for aldehyde and ketone removal.
Substrate (1.4 mmol) and aldehyde (1.4 mmol) were dissolved in 5 mL MeOH, 25 mL saturated NaHSO3(aq) added, shaken for approximately 30 s, diluted with 25 mL H2O, and extracted with 25 mL 10% EA/hexanes. The organic layer was dried (MgSO4), filtered, and concentrated in vacuo to yield the recovered substrate.
Work-up procedure for non-polar aldehyde and ketone removal.
Substrate (1.4 mmol) and aldehyde (1.4 mmol) were dissolved in 10 mL DMF, 25 mL saturated NaHSO3(aq) added, shaken for approximately 30 s, diluted with 25 mL H2O, and extracted with 25 mL 10% EA/hexanes. The aqueous layer was extracted with 25 mL of 10% EA/hexanes. The combined organic layers were washed three times with H2O (25 mL, 10 mL, 5 mL). The organic layer was dried (MgSO4), filtered, and concentrated in vacuo to yield the recovered substrate.
Work-up procedure for isolation of both aldehyde and ketone.
Benzyl butyrate (250 μL, 1.4 mmol) and aldehyde 20 (275.0 mg, 1.4 mmol) were dissolved in 10 mL DMF, 25 mL saturated NaHSO3(aq) added, shaken for approximately 30 s, diluted with 25 mL H2O, and extracted with 25 mL 10% EA/hexanes. The aqueous layer was extracted with 25 mL of 10% EA/hexanes three times. The organic layers were washed three times with H2O (25 mL, 10 mL, 5 mL). The organic layer was dried (MgSO4), filtered, and concentrated in vacuo to yield recovered benzyl butyrate (261.3 mg, 98% recovery). The combined aqueous layers were basified with 50% sodium hydroxide and extracted with 25 mL of 10% EA/hexanes three times. The organic layers were washed three times with H2O (25 mL, 10 mL, 5 mL). The organic layer was dried (MgSO4), filtered, and concentrated in vacuo to yield recovered aldehyde 20 (261.3 mg, 95% recovery).
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