Diazomethane → 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester

HRID 1576180Notes

Reaction equation

HRID 1576180 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[C:6](=[O:16])[C:5]=2[CH:4]=[CH:3][C:2]=1[CH:17]([CH3:21])[C:18]([OH:20])=[O:19].[N+](=[CH2:24])=[N-]>O1CCOCC1>[CH3:24][O:19][C:18](=[O:20])[CH:17]([C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:16])[C:7]3[CH:15]=[CH:14][CH:13]=[CH:12][C:8]=3[CH:9]=[CH:10][C:11]=2[CH:1]=1)[CH3:21]

Participants

4

Reactant 2

HCID 9550DiazomethaneHCID 1739105H-Dibenzo(a,d)cycloheptene-2-acetic acid, alpha-methyl-5-oxo-

Product 1

HCID 123988252-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

5.0 G. of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid (preparation described infra) is suspended in 50 ml. of dioxane, added to excess ethereal diazomethane and stirred until dissolution is complete and evaporated to dryness. Purification as in part A on silica gel affords a nearly quantitative yield of 2-(5H-dibenzo[a,d]cyclohepten-5-on-2-yl)propionic acid methyl ester as in part A.

Workup

  1. customevaporated to dryness
  2. customPurification as in part A on silica gel

Sources & evidence

ORD record
ord-94fc95de7e8b48e39d1c4d4512e965dc
Source dataset
uspto-grants-1976_09
Patent number
US03979430

Reaction notes

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