Oxalyl chloride → HCID 11424769, compound
Reaction equation
[CH3:1][C:2]1[C:7]2[CH2:8][CH2:9][CH:10]([C:14]([OH:16])=[O:15])[CH2:11][C:12](=[O:13])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C:17](Cl)(=O)C(Cl)=O>ClCCl>[CH3:17][O:15][C:14]([CH:10]1[CH2:9][CH2:8][C:7]2[C:2]([CH3:1])=[CH:3][CH:4]=[CH:5][C:6]=2[C:12](=[O:13])[CH2:11]1)=[O:16]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-methyl-5-oxo-6,7,8,9-tetrahydro-5H-benzocycloheptene-7-carboxylic acid (5 g, 22.91 mmol) in dry dichloromethane (DCM) (15 mL), oxalyl chloride (6 mL, 68.75 mmol) was added dropwise at 0° C. The reaction mixture was stirred overnight at room temperature, concentrated in vacuo and to the residue dissolved in DCM (30 mL), methanol (15 mL) was added at 0° C. After stirring 1.5 h at room temperature, the mixture was diluted with water (60 mL) and extracted with DCM (100 mL), the organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give 6.0 g of a yellow oil. Purification by flash chromatography on silica gel (hexane/diethyl ether: 8/2) afforded the title compound as a pale yellow oil (5.6 g, 94%).