2-Heptanone, 1-(triphenylphosphoranylidene)- → 2-(7-Hydroxyheptyl)-3-(3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol

HRID 442442Notes

Reaction equation

HRID 442442 reaction equation
[CH:1]([CH:3]1[CH2:7][CH:6]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:5]([OH:15])[CH:4]1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][OH:23])=O.[C:24]([CH:31]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29]>O1CCCC1>[OH:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH:4]1[CH:3]([CH:1]=[CH:31][C:24](=[O:30])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH2:7][CH:6]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][O:10]2)[CH:5]1[OH:15]

Participants

4

Reactant 2

HCID 107619442-Heptanone, 1-(triphenylphosphoranylidene)-HCID 203548513-Formyl-2-(7-hydroxyheptyl)-5-(2-tetrahydropyranyloxy)cyclopentanol

Product 1

HCID 867329952-(7-Hydroxyheptyl)-3-(3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanolYield 57.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-formyl-2-(7-hydroxyheptyl)-5-(2-tetrahydropyranyloxy)cyclopentanol [5.4 g.; prepared as described above in Example 2(e)] and hexanoylmethylene triphenylphosphorane (5.6g.) in dry tetrahydrofuran (60 ml.) was heated under reflux under nitrogen for 24 hours. The solvent was then removed in vacuo and the resulting residue was chromatographed on silica gel. Elution with diethyl ether gave 2-(7-hydroxyheptyl)-3-(3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol (3.64g.), νmax 3450 cm-1, 1670 cm-1, 1630 cm-1, 985 cm-1.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux under nitrogen for 24 hours
  3. customThe solvent was then removed in vacuo
  4. customthe resulting residue was chromatographed on silica gel
  5. washElution with diethyl ether

Sources & evidence

ORD record
ord-5082490ecc6a4c5baec8afff19a7cd99
Source dataset
uspto-grants-1977_08
Patent number
US04045467

Reaction notes

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