Benzoyl chloride → 2(S)-(benzoyloxymethyl)-1,3-oxathiolane

HRID 1689575ノート

反応式

HRID 1689575 の反応式
[OH:1][CH2:2][C@@H:3]1[S:7][CH2:6][CH2:5][O:4]1.[C:8](Cl)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C(N(CC)CC)C>ClCCl>[C:8]([O:1][CH2:2][C@@H:3]1[S:7][CH2:6][CH2:5][O:4]1)(=[O:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

参加物

5

反応物 3

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 46244897HCID 46244897、化合物

生成物 1

HCID 596089912(S)-(benzoyloxymethyl)-1,3-oxathiolane収率 44.6%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2(S)-(Hydroxymethyl)-1,3-oxathiolane (0.25 mmol, 30 mg, 1.0 equiv.) recovered from Example 3 was treated with benzoyl chloride (0.25 mmol, 35 mg, 1.0 equiv.), triethylamine (0.25 mmol, 25 mg, 1.0 equiv.) in dichloromethane (1 mL) at ambient temperature while monitoring the reaction progress by TLC. After 1 h, the reaction was extracted with saturated ammonium chloride solution and brine. The organic phase was concentrated and chromatographed on silica gel to give 2(S)-(benzoyloxymethyl)-1,3-oxathiolane (25 mg, 44.6%).

後処理

  1. extractionthe reaction was extracted with saturated ammonium chloride solution and brine
  2. concentrationThe organic phase was concentrated
  3. customchromatographed on silica gel

出典と根拠

ORDレコード
ord-2b1d43f87cb148e4864d59d7e1a195a5
出典データセット
uspto-grants-2012_04
特許番号
US08153416B2

反応ノート

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