2-Heptanone, 1-(triphenylphosphoranylidene)- → 2-(7-Hydroxyheptyl)-3-(3-oxo-1-octenyl)cyclopentanol

HRID 1581092Notes

Reaction equation

HRID 1581092 reaction equation
[OH:1][CH:2]1[CH2:6][CH2:5][CH:4]([CH:7]=O)[CH:3]1[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][OH:16].[C:17]([CH:24]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22]>O1CCCC1>[OH:16][CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH:3]1[CH:4]([CH:7]=[CH:24][C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:5][CH2:6][CH:2]1[OH:1]

Participants

4

Reactant 2

HCID 107619442-Heptanone, 1-(triphenylphosphoranylidene)-HCID 215614973-Hydroxy-2-(7-hydroxyheptyl)cyclopentane-1-carbaldehyde

Product 1

HCID 737960592-(7-Hydroxyheptyl)-3-(3-oxo-1-octenyl)cyclopentanolYield 63%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-hydroxy-2-(7-hydroxyheptyl)cyclopentanecarbaldehyde (4.5 g., 0.02 mole) and hexanoylmethylene triphenylphosphorane (7.5 g., 0.02 mole) in dry tetrahydrofuran (100 ml.) was heated under reflux for 6 hours. The solvent was removed in vacuo and the residue was chromatographed on silica gel. Elution with a 3:2 mixture of petrol (b.p. 40°-60°C.) and ethyl acetate gave 2-(7-hydroxyheptyl)-3-(3-oxo-1-octenyl)cyclopentanol (4 g., 63%), λmax 230 mμ, ε 12,900 (ethanol), νmax 1660 cm-1, 1620 cm-1 (liquid film).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue was chromatographed on silica gel
  5. washElution
  6. additionwith a 3:2 mixture of petrol (b.p. 40°-60°C.) and ethyl acetate

Sources & evidence

ORD record
ord-650faa6d3108440898981a376dac7454
Source dataset
uspto-grants-1976_01
Patent number
US03935261

Reaction notes

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