Diazomethane → HCID 21702035, compound

HRID 1596405Notes

Reaction equation

HRID 1596405 reaction equation
[N+](=[CH2:3])=[N-].[OH:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([O:14][CH2:15][CH3:16])[CH:9]=1)=[O:7]>CCOCC>[CH2:15]([O:14][C:10]1[CH:9]=[C:8]([C:6](=[O:7])[CH2:5][O:4][CH3:3])[CH:13]=[CH:12][CH:11]=1)[CH3:16]

Participants

4

Reactant 2

HCID 9550Diazomethane2×HCID 21702034HCID 21702034, compound2×

Product 1

HCID 21702035HCID 21702035, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent3×

Procedure

Boron trifluoride-diethyl ether complex (3 drops) and an ether solution of diazomethane were added to a solution of 2-hydroxy-3′-ethoxyacetophenone (1.6 g, 8.9 m mol) in ether (60 ml). The ether solution of diazomethane was added until thin-layer reveals that the spot of 2-hydroxy-3′-ethoxyacetophenone has disappeared. After insoluble matter was filtered off, the filtrate was concentrated under reduced pressure. The resulting residue was subjected to chromatography on silica gel (40 g) using ethyl acetate-hexane (1:4). Thus, the desired compound (1.13 g, 65%) was obtained as a colorless oily material.

Workup

  1. filtrationAfter insoluble matter was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-577e3dcba3f445b9b0868671b490c467
Source dataset
uspto-grants-2001_09
Patent number
US06291485B1

Reaction notes

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