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

HRID 496999ノート

反応式

HRID 496999 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-d8dfd62967db42498476675a65d5d555
出典データセット
uspto-grants-2005_09
特許番号
US06949529B2

反応ノート

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