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

HRID 2062177Notes

Reaction equation

HRID 2062177 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  1. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-faaae9397228433ba372fb9d7750843f
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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