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

HRID 2062177

반응식

HRID 2062177 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 22876378(3S)-oxolan-3-yl carbonochloridate수율 85%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  1. customthe solvent was removed under vacuum

출처 및 근거

ORD 기록
ord-faaae9397228433ba372fb9d7750843f
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08283354B2

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