Oxalyl chloride → HCID 11424769, compound

HRID 1354572Notes

Reaction equation

HRID 1354572 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

HCID 65578Oxalyl chlorideHCID 11229708HCID 11229708, compound

Product 1

HCID 11424769HCID 11424769, compoundYield 112.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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%).

Workup

  1. concentrationconcentrated in vacuo and to the residue
  2. dissolutiondissolved in DCM (30 mL)
  3. additionmethanol (15 mL) was added at 0° C
  4. stirringAfter stirring 1.5 h at room temperature
  5. additionthe mixture was diluted with water (60 mL)
  6. extractionextracted with DCM (100 mL)
  7. dry with materialthe organic layer was dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dafe0e9d668045258f4adb3ee86ec2e8
Source dataset
uspto-grants-2007_05
Patent number
US07223867B2

Reaction notes

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