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

HRID 2062225

Reaction equation

HRID 2062225 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 641512(-)-3-Hydroxytetrahydrofuran

Product 1

HCID 58089797(3R)-oxolan-3-yl carbonochloridateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of (R)-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 (R)-tetrahydrofuran-3-yl chloroformate (12.1 g, 85%) as a clear liquid.

Workup

  1. customthe solvent was removed under vacuum

Sources & evidence

ORD record
ord-c886714fc2fa4417947d8e510db17166
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Linked notes

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