Sodium hydride → 6-(7-Hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane

HRID 2286062Notes

Reaction equation

HRID 2286062 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[CH2:30][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>[OH:38][CH2:37][CH2:36][CH2:35][CH2:34][CH2:33][CH2:32][CH2:31][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])[CH2:30][CH2:29][C:24]21[O:25][CH2:26][CH2:27][O:28]2

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 12906670Dimethyl 2-Oxo-3-methylheptylphosphonateHCID 205428916-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehydeHCID 178418361HCID 178418361, compound

Product 1

HCID 570760486-(7-Hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent3×

Procedure

Dimethyl 3-methyl-2-oxoheptylphosphonate (5.1 g; prepared as described in the Specification of Netherlands Patent Application No. 7203126) in dry tetrahydrofuran (20 ml.) was added dropwise to a stirred suspension of sodium hydride (0.52 g.) in dry tetrahydrofuran (150 ml.) at ambient temperature under nitrogen. The reaction mixture was stirred at ambient temperature until hydrogen evolution had ceased, and then treated with a solution of 7-formyl-6-(7-hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (5.1 g.) in dry tetrahydrofuran (50 ml.). After stirring for a further period of 2 hours at ambient temperature the reaction mixture was acidified to pH 4 with glacial acetic acid and then concentrated under reduced pressure. The residue was triturated with diethyl ether and filtered. The filtrate was washed with dilute aqueous sodium carbonate solution and water respectively, then dried over sodium sulphate. Removal of the solvent under reduced pressure gave crude 6-(7-hydroxyheptyl)-7-(4-methyl-3-oxooct-1-enyl)-1,4-dioxaspiro[4,4]nonane (7.6 g.), νmax (liquid film) 3450 cm-1, 1680 cm-1, 1660 cm-1, 1620 cm-1, 1380 cm-1, 1040 cm-1, which was used in the next stage without further purification being necessary.

Workup

  1. customprepared
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was triturated with diethyl ether
  4. filtrationfiltered
  5. washThe filtrate was washed with dilute aqueous sodium carbonate solution and water respectively
  6. dry with materialdried over sodium sulphate
  7. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-3fe2b9ea7a96456ab751308d2ddddafa
Source dataset
uspto-grants-1982_04
Patent number
US04325967

Reaction notes

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