Dimethyl Sulfoxide → 3-o-t-Butyldimethylsilyl-2-o-methyl-rac-glyceraldehyde

HRID 496999노트

반응식

HRID 496999 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[Si:11]([O:18][CH2:19][CH:20]([CH2:23][OH:24])[O:21][CH3:22])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl>[Si:11]([O:18][CH2:19][CH:20]([O:21][CH3:22])[CH:23]=[O:24])([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:12])[CH3:13]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 223164511-o-t-Butyldimethylsilyl-2-o-methyl-rac-glycerol

생성물 1

HCID 543075043-o-t-Butyldimethylsilyl-2-o-methyl-rac-glyceraldehyde

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of oxalyl chloride (87 μL, 1.0 mmol) in CH2Cl2 (7 mL) at −78° C. was added DMSO (71 μL, 1.0 mmol). After 20 min, alcohol Compound 42 (0.20 g, 0.91 mmol) was added followed, after another 20 min, by the addition of triethylamine (0.63 mL, 4.6 mmol). The reaction was warmed to room temperature over a 10 min period, filtered through a plug of silica-gel, which was washed with ethyl acetate (50 mL) and concentrated to give 3-O-t-butyldimethylsilyl-2-O-methyl-rac-glyceraldehyde Compound 73 (0.20 g, 100%) as a colourless oil.

후처리

  1. filtrationfiltered through a plug of silica-gel, which
  2. washwas washed with ethyl acetate (50 mL)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d8dfd62967db42498476675a65d5d555
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06949529B2

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