Reaction #3777

ord-1ed77840c3734a39844b39f7948bc2ab

Reaction equation

c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CCOC(=O)C(C)(C)CCCOc1ccc(OCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-]
3-[4-(4,4-dimethyl-4-ethoxycarbonylbutoxy)phenoxy]propyltriphenylphosphonium bromide
CCOC(=O)C(C)(C)CCCOc1ccc(OCCCBr)cc1
ethyl 2,2-dimethyl-5-[4-(3-bromopropyloxy)phenoxy]pentanoate
→
CCOC(=O)CCCCOc1ccc(OCCCO)cc1
ethyl 5-[4-(3-hydroxypropyloxy)phenoxy]pentanoate
BrBr
bromine
c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine

Reactants

c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphine
CCOC(=O)C(C)(C)CCCOc1ccc(OCCC[P+](c2ccccc2)(c2ccccc2)c2ccccc2)cc1.[Br-]
3-[4-(4,4-dimethyl-4-ethoxycarbonylbutoxy)phenoxy]propyltriphenylphosphonium bromide
CCOC(=O)C(C)(C)CCCOc1ccc(OCCCBr)cc1
ethyl 2,2-dimethyl-5-[4-(3-bromopropyloxy)phenoxy]pentanoate

Reagents

None

Solvents

CC#N
acetonitrile
CC#N
acetonitrile

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherwas prepared

Procedure

The 3-[4-(4,4-dimethyl-4-ethoxycarbonylbutoxy)phenoxy]propyltriphenylphosphonium bromide used as starting material was prepared by reacting triphenylphosphine in acetonitrile, at reflux, with ethyl 2,2-dimethyl-5-[4-(3-bromopropyloxy)phenoxy]pentanoate, itself obtained from ethyl 5-[4-(3-hydroxypropyloxy)phenoxy]pentanoate and bromine in acetonitrile in the presence of triphenylphosphine.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05734077uspto-grants-1998_03