6-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehyde → 6-(7-Hydroxyhepty)-7-(3-oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[4,4]nonane

HRID 259200Notes

Reaction equation

HRID 259200 reaction equation
[CH:1]([CH:3]1[CH2:11][CH2:10][C:5]2([O:9][CH2:8][CH2:7][O:6]2)[CH:4]1[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])=O.[CH2:20]([O:23][CH2:24][C:25]([CH:27]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:26])[CH2:21][CH3:22]>O1CCCC1>[OH:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][CH:4]1[CH:3]([CH:1]=[CH:27][C:25](=[O:26])[CH2:24][O:23][CH2:20][CH2:21][CH3:22])[CH2:11][CH2:10][C:5]21[O:9][CH2:8][CH2:7][O:6]2

Participants

4

Reactant 2

HCID 205428916-(7-Hydroxyheptyl)-1,4-dioxaspiro[4.4]nonane-7-carbaldehydeHCID 21423422Propoxyacetylmethylenetriphenylphosphorane

Product 1

HCID 572413446-(7-Hydroxyhepty)-7-(3-oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[4,4]nonaneYield 150.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-formyl-6-(7 -hydroxyheptyl)-1,4-dioxaspiro[4,4]nonane (4.2 g.) and propoxyacetylmethylenetriphenylphosphorane (7.18 g.) in dry tetrahydrofuran (35 ml.) was heated at reflux under nitrogen for 18 hours. The solvent was removed in vacuo and the residue triturated with a mixture of petroleum ether (b.p. 60°-80° C.) and ethyl acetate, allowed to stand at 0° C., filtered to remove triphenylphosphine oxide and the filtrate evaporated to dryness to give 6-(7-hydroxyheptyl)- 7-(3-oxo-4 -propoxybut-1-enyl)-1,4-dioxaspiro[4,4]nonane (8.6 g.), νmax 1620 cm-1, 1680 cm-1.

Workup

  1. temperaturewas heated
  2. temperatureat reflux under nitrogen for 18 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue triturated with a mixture of petroleum ether (b.p. 60°-80° C.) and ethyl acetate
  5. customto stand at 0° C.
  6. filtrationfiltered
  7. customto remove triphenylphosphine oxide
  8. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-8568b0be4b6d4daba554faf830c6f4a8
Source dataset
uspto-grants-1977_07
Patent number
US04036872

Reaction notes

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