Phenylmethyl hydrogen carbonate → Benzyloxyacetyl chloride

HRID 415675Notes

Reaction equation

HRID 415675 reaction equation
[CH2:1]([O:8][C:9](=O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)[C:13]([Cl:15])=[O:14]>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][CH2:9][C:13]([Cl:15])=[O:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 2285Phenylmethyl hydrogen carbonateHCID 65578Oxalyl chloride

Product 1

HCID 177085Benzyloxyacetyl chlorideYield 96%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of carbonic acid monobenzyl ester (3.50 g, 21.0 mmol) in the 50 ml of DCM and 0.50 ml of DMF was cooled to −78° C. followed by addition of oxalyl chloride (11.79 ml, 105 mmol). The resulting reaction mixture was stirred at room temperature for 1 h. After the completion of the reaction mixture (TLC monitoring), concentrated it to give 2-benzyloxyacetyl chloride (3.0 g, 96%). To an ice cold solution of 3-amino-4-chloro-benzoic acid methyl ester in 10 ml of DCM was added triethylamine (2.47 ml, 17.78 mmol) followed by addition of 2-benzyloxyacetyl chloride (3.0 g, 17.78 mmol) in 10 ml of DCM. The reaction mixture was stirred at 25° C. for 12 hr. After the completion of the reaction mixture (TLC monitoring), the reaction mixture was evaporated to dryness under reduced pressure. The residue was purified by column chromatography on silica (60-120 M) using ethyl acetate/hexane (5:95) as the eluent to provide the title compound (1.70 g, 31%).

Workup

  1. customThe resulting reaction mixture
  2. concentrationAfter the completion of the reaction mixture (TLC monitoring), concentrated it

Sources & evidence

ORD record
ord-130dceff71c3491fbab2f5a7933fe10f
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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