TRANS 5-(t-BUTYLDIPHENYLSILYLOXYMETHYL)-2-(DIETHYLOXYPHOSPHINOYL)-1,3-OXATHIOLANE → Trans-2-(Diethyloxyphosphinoyl)-5-Hydroxymethyl-1,3-Oxathiolane

HRID 365768ノート

反応式

HRID 365768 の反応式
[Si]([O:18][CH2:19][C@@H:20]1[O:24][C@@H:23]([P:25]([O:30][CH2:31][CH3:32])([O:27][CH2:28][CH3:29])=[O:26])[S:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1>CO.C(Cl)(=O)C.[Cl-].[NH4+]>[CH2:28]([O:27][P:25]([O:30][CH2:31][CH3:32])([C@H:23]1[S:22][CH2:21][C@H:20]([CH2:19][OH:18])[O:24]1)=[O:26])[CH3:29]

参加物

5

反応物 1

HCID 131720781TRANS 5-(t-BUTYLDIPHENYLSILYLOXYMETHYL)-2-(DIETHYLOXYPHOSPHINOYL)-1,3-OXATHIOLANE

生成物 1

HCID 86752984Trans-2-(Diethyloxyphosphinoyl)-5-Hydroxymethyl-1,3-Oxathiolane収率 80%

試薬・触媒・溶媒 3

HCID 6367Acetyl chloride触媒HCID 25517Ammonium Chloride触媒HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

To a solution of cis and trans-5-t-butyldimethylsilyloxymethyl-2-(diethyloxyphosphinoyl)-1,3-oxathiolane (example 25) (4.00 g, 10.8 mmol) in MeOH (30 mL) was added a few drops of acetyl chloride (200 μL) at 0° C. The mixture was stirred at 0° C. for 1 hr. and at room temperature for 18 hr. A few drops of ammonium chloride was added and the solvent was evaporated under reduced pressure. The crude material was purified by several flash chromatography with a mixture of dichloromethane and methanol (96:4) to give 382 mg of the cis isomer, 1.19 g of the trans isomer and 332 mg of the mixture in a total yield of 80% after the first purification.

後処理

  1. waitand at room temperature for 18 hr
  2. customthe solvent was evaporated under reduced pressure
  3. customThe crude material was purified by several flash chromatography with a mixture of dichloromethane and methanol (96:4)

出典と根拠

ORDレコード
ord-d923bee19ebb421e87e0509191594c07
出典データセット
uspto-grants-2000_10
特許番号
US06127540

反応ノート

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