Sodium hydride → 7-(3-Cyclohexyl-3-oxoprop-1-enyl)-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane

HRID 372057Notes

Reaction equation

HRID 372057 reaction equation
[CH:1]1([C:7](=[O:15])[CH2:8]P(=O)(OC)OC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[H][H].[CH:20]([CH:22]1[CH2:30][CH2:29][C:24]2([O:28][CH2:27][CH2:26][O:25]2)[CH:23]1[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38])=O>O1CCCC1.C(O)(=O)C>[CH:1]1([C:7](=[O:15])[CH:8]=[CH:20][CH:22]2[CH2:30][CH2:29][C:24]3([O:25][CH2:26][CH2:27][O:28]3)[CH:23]2[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][OH:38])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 13187487Dimethyl (2-cyclohexyl-2-oxoethyl)phosphonateHCID 205428916-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 570271747-(3-Cyclohexyl-3-oxoprop-1-enyl)-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonaneYield 112%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of dimethyl 2-cyclohexyl-2-oxoethylphosphonate (10.1 g.) in dry tetrahydrofuran (40 ml.) was added to a stirred suspension of sodium hydride (1.04 g.) in dry tetrahydrofuran (300 ml.). The mixture was stirred at room temperature until the evolution of hydrogen had ceased, then treated dropwise with a solution of 7-formyl-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane [10.2 g; prepared as described in Example 1(iv) above] in dry tetrahydrofuran (100 ml.) and stirred for a further 2 hours. The mixture was acidified to pH 4 by the addition of glacial acetic acid, the solvents were removed in vacuo, the residue was triturated with diethyl ether and the solid filtered off. The ethereal solution was washed with aqueous sodium carbonate solution, dried over magnesium sulphate, and evaporated to dryness, to give 7-(3-cyclohexyl-3-oxoprop-1-enyl)-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (16 g.), νmax 3400 cm-1, 1680 cm-1, 1650 cm-1, 1620 cm-1, 1040 cm-1.

Workup

  1. customthe solvents were removed in vacuo
  2. customthe residue was triturated with diethyl ether
  3. filtrationthe solid filtered off
  4. washThe ethereal solution was washed with aqueous sodium carbonate solution
  5. dry with materialdried over magnesium sulphate
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-d112a2ec1f574dce8eb9740f973c11bd
Source dataset
uspto-grants-1978_05
Patent number
US04088695

Reaction notes

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