Propyltriphenylphosphonium bromide → 3-(2-Pentenyl)-cyclopentanol

HRID 615836Notes

Reaction equation

[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH2:7][CH:8]=O)[CH2:3]1.[Br-].[C:11]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)CCC)[CH:16]=CC=C[CH:12]=1>>[CH2:7]([CH:4]1[CH2:5][CH2:6][CH:2]([OH:1])[CH2:3]1)[CH:8]=[CH:12][CH2:11][CH3:16]

Participants

Reactant 2

HCID 80374Propyltriphenylphosphonium bromide

HCID 537697943-Hydroxy cyclopentyl-acetaldehyde

Product 1

HCID 538336653-(2-Pentenyl)-cyclopentanolYield 24.9%

Procedure

Using the procedure of Example 3, 5 g of 3-hydroxy cyclopentyl-acetaldehyde and 20 g of triphenyl propyl phosphonium bromide were reacted and the product was chromatographed over silica gel. Elution with a 7-3 cyclohexane-ethyl acetate mixture yielded 1.5 g of 3-(2-pentenyl)-cyclopentanol.

Workup

customwere reacted
customthe product was chromatographed over silica gel
washElution with a 7-3 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record: ord-54177a6b356f4f33835c4dcada38cd6c
Source dataset: uspto-grants-1985_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04501687

Reaction notes

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