Oxalyl chloride → HCID 57941380, compound
Reaction equation
[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].[CH3:7][C@@:8]12[C:14]([CH3:16])([CH3:15])[C@@H:11]([CH2:12][CH2:13]1)C(C(O)=O)[C:9]2=[O:20]>CN(C)C=O.ClCCl>[CH3:7][C@@:8]12[C:14]([CH3:16])([CH3:15])[C@@H:11]([CH2:12][CH2:13]1)[CH:1]([C:2]([Cl:4])=[O:3])[C:9]2=[O:20]Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 0 °C
Procedure
Oxalyl chloride (2.8 mL, 32.1 mmol) was added over a period of 10 min to a solution of (1S,4S)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carboxylic acid (Intermediate 24; 2.1 g, 10.7 mmol) and N,N-dimethylformamide (3 drops) in dichloromethane (15 mL) at 0° C. The reaction mixture was stirred at 0° C. for 5 min and then at room temperature for 2 h. The solvent was evaporated, and the residue was co-evaporated three times with dichloromethane and then dried under high vacuum for 20 min to give (1S,4S)-4,7,7-trimethyl-3-oxo-bicyclo[2.2.1]heptane-2-carbonyl chloride (2.2 g, 96%) as an orange oil. This was used directly in subsequent steps without further purification.
Workup
- waitat room temperature for 2 h
- customThe solvent was evaporated
- customdried under high vacuum for 20 min
Sources & evidence
- ORD record
- ord-09d92524ddaf4166b2601d102433de23
- Source dataset
- uspto-grants-2009_11
- Patent number
- US07622492B2
Reaction notes
Loading…