Sodium hydride → 2-(7-Hydroxyheptyl)-3-(4-methyl-3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol

HRID 442448Notes

Reaction equation

HRID 442448 reaction equation
[CH3:1][CH:2]([CH2:12][CH2:13][CH2:14][CH3:15])[C:3](=[O:11])[CH2:4]P(=O)(OC)OC.[H-].[Na+].[H][H].[CH:20]([CH:22]1[CH2:26][CH:25]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH:24]([OH:34])[CH:23]1[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][OH:42])=O>O1CCCC1.C(O)(=O)C>[OH:42][CH2:41][CH2:40][CH2:39][CH2:38][CH2:37][CH2:36][CH2:35][CH:23]1[CH:22]([CH:20]=[CH:4][C:3](=[O:11])[CH:2]([CH3:1])[CH2:12][CH2:13][CH2:14][CH3:15])[CH2:26][CH:25]([O:27][CH:28]2[CH2:33][CH2:32][CH2:31][CH2:30][O:29]2)[CH:24]1[OH:34]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 12906670Dimethyl 2-Oxo-3-methylheptylphosphonateHCID 203548513-Formyl-2-(7-hydroxyheptyl)-5-(2-tetrahydropyranyloxy)cyclopentanolHCID 178418361HCID 178418361, compound

Product 1

HCID 867350452-(7-Hydroxyheptyl)-3-(4-methyl-3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanolYield 93.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of dimethyl 3-methyl-2-oxoheptylphosphonate (2.36 g.) in tetrahydrofuran (20 ml.) was added dropwise to a stirred suspension of sodium hydride (0.24 g.) in tetrahydrofuran (50 ml.). The mixture was stirred at room temperature until the evolution of hydrogen has ceased, then treated dropwise with a solution of 3-formyl-2-(7-hydroxyheptyl)-5-(2-tetrahydropyranyloxy)cyclopentanol [3.28 g.; prepared as described above in Example 2(e)] in tetrahydrofuran (20 ml.) and stirred for a further 2 hours. The mixture was acidified to pH 4 by the addition of glacial acetic acid, the solvent was removed in vacuo and the residue dissolved in diethyl ether. The ethereal solution was washed with aqueous sodium carbonate solution, dried over magnesium sulphate, and evaporated to dryness to give 2-(7-hydroxyheptyl)-3-(4-methyl-3-oxooct-1-enyl)-5-(2-tetrahydropyranyloxy)cyclopentanol (4.1 g.).

Workup

  1. customthe solvent was removed in vacuo
  2. dissolutionthe residue dissolved in diethyl ether
  3. washThe ethereal solution was washed with aqueous sodium carbonate solution
  4. dry with materialdried over magnesium sulphate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-d20a619bcf564cc3bb8e5ccc4b3c392f
Source dataset
uspto-grants-1977_08
Patent number
US04045467

Reaction notes

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