Oxalyl chloride → HCID 86625245, compound

HRID 2353064Notes

Reaction equation

HRID 2353064 reaction equation
[C:1]1([C:7]23[CH2:14][CH2:13][C:10]([C:15]([OH:17])=O)([CH2:11][CH2:12]2)[CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(Cl)(=O)C([Cl:21])=O>C(Cl)Cl.CN(C=O)C>[C:1]1([C:7]23[CH2:14][CH2:13][C:10]([C:15]([Cl:21])=[O:17])([CH2:11][CH2:12]2)[CH2:9][CH2:8]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 126177784-Phenylbicyclo[2.2.2]octane-1-carboxylic acid

Product 1

HCID 86625245HCID 86625245, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To an ice-water cooled solution of 4-phenylbicyclo[2.2.2]octane-1-carboxylic acid (479 mg, 2.07 mmol) in DCM (20 mL) was added DMF (2-3 drops) followed by oxalyl chloride (0.20 mL, 2.14 mmol). The reaction mixture was allowed to warm to ambient temperature overnight and then solvent was evaporated under reduced pressure to leave crude 4-phenylbicyclo[2.2.2]octane-1-carbonyl chloride which was used directly in the next stage.

Workup

  1. customsolvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-281cff9cd67b491fb757a24932bba11a
Source dataset
uspto-grants-2010_07
Patent number
US07749997B2

Reaction notes

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