Oxalyl chloride → (2E)-3-cyclopentylacryloyl chloride
Reaction equation
[CH:1]1(/[CH:6]=[CH:7]/[C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.C(Cl)(=O)C([Cl:14])=O>C(Cl)Cl>[CH:1]1(/[CH:6]=[CH:7]/[C:8]([Cl:14])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of (2E)-3-cyclopentylacrylic acid (1.3 g, 9.3 mmol) in DCM (65 mL) at 0° C. was added oxalyl chloride (3.1 mL, 37 mmol), dropwise. The resulting solution was stirred at 0° C. for 40 minutes, then at room temperature for 2 hours. The volatiles were evaporated to afford (2E)-3-cyclopentylacryloyl chloride as a colorless liquid. A portion of this (2E)-3-cyclopentylacryloyl chloride (0.75 g, 4.7 mol) was dissolved in methanol (10 mL) and the resulting solution was stirred for 2 hours. The solvent was evaporated to afford the product (700 mg, 96%).
Workup
- waitat room temperature for 2 hours
- customThe volatiles were evaporated
Sources & evidence
- ORD record
- ord-bc3c6b1191974c64bd07702de2af37c3
- Source dataset
- uspto-grants-2013_09
- Patent number
- US08541425B2
Reaction notes
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