Methanol → methyl (S)-3-trityloxy-2-methylpropionate

HRID 654989ノート

反応式

HRID 654989 の反応式
[CH3:1][C@@H:2]([CH2:7][OH:8])[C:3]([O:5][CH3:6])=[O:4].[C:9](Cl)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CO.O>CN(C)C=O>[C:9]([O:8][CH2:7][C@H:2]([CH3:1])[C:3]([O:5][CH3:6])=[O:4])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

参加物

6

反応物 4

HCID 887MethanolHCID 962WaterHCID 6456Trityl chloride2 回HCID 10192563methyl (2S)-3-hydroxy-2-methylpropanoate

生成物 1

HCID 11728102methyl (S)-3-trityloxy-2-methylpropionate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Methyl (S)-(+)-2-methyl-3-hydroxypropionate (1.18 g; 10 mmole), trityl chloride (3.1 g; 11.13 mmole) and N,N-dimethylaminopyridine (1.34 g; 11 mmole) were dissolved in dry dimethylformamide (10 ml), and the resultant mixture was stirred at room temperature overnight. Methanol (5 ml) was added thereto to decompose the unreacted trityl chloride, and the resultant mixture was stirred for 3 hours. Water (20 ml) was added to the reaction mixture, which was extracted with toluene (20 ml) three times. The extracts were combined together, washed with water, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give methyl (S)-3-trityloxy-2-methylpropionate.

後処理

  1. extractionwas extracted with toluene (20 ml) three times
  2. washwashed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-3691e7a8fbd447b8905dcef4a3728266
出典データセット
uspto-grants-1992_07
特許番号
US05134231

反応ノート

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