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
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]2Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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.