Trimethylsilyldiazomethane → Methyl 3-chlorocyclobutanecarboxylate

HRID 595320Notes

Reaction equation

HRID 595320 reaction equation
[Si](C=[N+]=[N-])(C)(C)[CH3:2].[Cl:8][CH:9]1[CH2:12][CH:11]([C:13]([OH:15])=[O:14])[CH2:10]1>CO.ClCCl>[Cl:8][CH:9]1[CH2:12][CH:11]([C:13]([O:15][CH3:2])=[O:14])[CH2:10]1

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 138154143-Chlorocyclobutane-1-carboxylic acid

Product 1

HCID 13815415Methyl 3-chlorocyclobutanecarboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

TMS-diazomethane (2.0 M in diethyl ether, 2.2 ml, 4.4 mmol) was added dropwise to a solution of 3-chlorocyclobutanecarboxylic acid (540 mg, 4.0 mmol) in methanol (5.0 mL) and dichloromethane (5.0 mL) at 0° C. The reaction mixture was concentrated under reduced pressure to afford methyl 3-chlorocyclobutanecarboxylate. The material was used in the subsequent reaction without purification.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2461b7a55ae240a3bcfe584ae2661436
Source dataset
uspto-grants-2016_01
Patent number
US09242984B2

Reaction notes

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