Diazomethane → 10-Hydroxy-8-fluoro-dibenzo[b,f]thiepin-3-carboxylic acid methyl ester

HRID 1156152Notes

Reaction equation

HRID 1156152 reaction equation
[OH:1][C:2]1[C:8]2[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:14]=[C:15]([C:18]([OH:20])=[O:19])[CH:16]=[CH:17][C:4]=2[CH:3]=1.[N+](=[CH2:23])=[N-]>CO.CCOCC>[CH3:23][O:19][C:18]([C:15]1[CH:16]=[CH:17][C:4]2[CH:3]=[C:2]([OH:1])[C:8]3[CH:9]=[C:10]([F:13])[CH:11]=[CH:12][C:7]=3[S:6][C:5]=2[CH:14]=1)=[O:20]

Participants

5

Reactant 2

HCID 9550DiazomethaneHCID 2053699310-Hydroxy-8-fluoro-dibenzo[b,f]thiepin-3-carboxylic acid

Product 1

HCID 7054884210-Hydroxy-8-fluoro-dibenzo[b,f]thiepin-3-carboxylic acid methyl esterYield 78%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

10-Hydroxy-8-fluoro-dibenzo[b,f]thiepin-3-carboxylic acid (4 g; 13.8 mmoles) dissolved in methanol (100 mL) and treated with excess diazomethane in ether. The volatiles removed under vacuum and the residue, taken up in chloroform, is purified by chromatography in Silica Gel. Elution with 20% ethyl acetate in toluene yielded 3.26 g (78%) of the title compound, m.p. 85°-88° C.

Workup

  1. customThe volatiles removed under vacuum
  2. customis purified by chromatography in Silica Gel
  3. washElution with 20% ethyl acetate in toluene

Sources & evidence

ORD record
ord-d4e1d0a2e9894b4cb1b9ba607b28ebab
Source dataset
uspto-grants-1982_06
Patent number
US04334077

Reaction notes

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