Chloroacetyl chloride → 7-Octynyl 2-chloroacetate

HRID 415581

Reaction equation

HRID 415581 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

HCID 6577Chloroacetyl chlorideHCID 701007-Octyn-1-ol

Product 1

HCID 866432727-Octynyl 2-chloroacetateYield 111%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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

  1. customThe solvent was removed under reduced pressure
  2. customthe residue was purified by column chromatography on silica eluting with EtOAc/hexane (10%)

Sources & evidence

ORD record
ord-a53ce2f0785149c5a55641699c1c4594
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Linked notes

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