Toluene → (3S)-oxolan-3-yl carbonochloridate

HRID 2062177

反応式

HRID 2062177 の反応式
[O:1]1[CH2:5][CH2:4][C@H:3]([OH:6])[CH2:2]1.[C:7](Cl)([Cl:9])=[O:8].C1(C)C=CC=CC=1>C(Cl)Cl>[Cl:9][C:7]([O:6][C@H:3]1[CH2:4][CH2:5][O:1][CH2:2]1)=[O:8]

参加物

5

反応物 3

HCID 1140TolueneHCID 6371PhosgeneHCID 2733227(S)-(+)-3-Hydroxytetrahydrofuran

生成物 1

HCID 22876378(3S)-oxolan-3-yl carbonochloridate収率 85%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A stirred solution of (S)-tetrahydrofuran-3-ol (7.9 g, 90 mmol) in anhydrous CH2Cl2 (50 mL) under an N2 atmosphere was cooled in an ice bath, and a 20% solution of phosgene in toluene (134 mL, 270 mmol) was slowly added. The reaction was allowed to warm to room temperature overnight, and the solvent was removed under vacuum to afford (S)-tetrahydrofuran-3-yl chloroformate (12.1 g, 85%) as a clear liquid. 1H NMR (400 MHz, CDCl3) δ 5.42-5.39 (m, 1H), 4.01-3.84 (m, 4H), 2.31-2.13 (m, 2H).

後処理

  1. customthe solvent was removed under vacuum

出典と根拠

ORDレコード
ord-faaae9397228433ba372fb9d7750843f
出典データセット
uspto-grants-2012_10
特許番号
US08283354B2

関連ノート

読み込み中…