Oxalyl chloride → Hexahydro-2,5-methano-pentalene-3a-carbonyl chloride

HRID 1469930Notes

Reaction equation

HRID 1469930 reaction equation
[CH2:1]1[CH:8]2[C:4]3([C:10]([OH:12])=O)[CH2:5][CH:6]([CH2:9][CH:2]1[CH2:3]3)[CH2:7]2.C(Cl)(=O)C([Cl:16])=O>ClCCl>[CH2:1]1[CH:8]2[C:4]3([C:10]([Cl:16])=[O:12])[CH2:5][CH:6]([CH2:9][CH:2]1[CH2:3]3)[CH2:7]2

Participants

4

Reactant 2

HCID 65578Oxalyl chlorideHCID 2733865Hexahydro-2,5-methanopentalene-3a(1H)-carboxylic acid

Product 1

HCID 13182402Hexahydro-2,5-methano-pentalene-3a-carbonyl chlorideYield 99.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of commercially available hexahydro-2,5-methano-pentalene-3a-carboxylic acid (10 g, 0.06 mol) in dichloromethane (200 mL) was added oxalyl chloride (8.7 g, 0.066 mol). The mixture was stirred overnight and then concentrated under reduced pressure to afford the title compound as a colorless oil (11 g, 99%). MS (DCI/NH3) m/z 184 (M+H)+.

Workup

  1. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4f72d9e2f0384ffe856c5ab4ac0c50e1
Source dataset
uspto-grants-2015_04
Patent number
US09006275B2

Reaction notes

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