Chloroacetyl chloride → 7-Octynyl 2-chloroacetate
Reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[CH2:6]([OH:14])[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[CH:13]>C(Cl)Cl>[Cl:1][CH2:2][C:3]([O:14][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]#[CH:13])=[O:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Chloroacetyl chloride (0.16 ml, 2.0 mmol, 1 equiv.) was added to a stirred solution of 7-Octyn-1-ol (300 mg, 2.4 mmol, 1.2 equiv.) in CH2Cl2 (6 m-) at −5° C. The reaction mixture was allowed to warm-up to r.t., were it was stirred for 4 h. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica eluting with EtOAc/hexane (10%) to give the desired compound as a pale yellow liquid (450 mg, 100%).
Workup
- customThe solvent was removed under reduced pressure
- customthe residue was purified by column chromatography on silica eluting with EtOAc/hexane (10%)
Sources & evidence
- ORD record
- ord-c83d21f28a4f4056a459fd4038f3d72e
- Source dataset
- uspto-grants-2014_10
- Patent number
- US08865736B2
Reaction notes
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