2-Heptanone, 1-(triphenylphosphoranylidene)- → 6-(7-Hydroxyheptyl)-7-(5-ethoxy-3-oxopent-1-enyl)-1,4-dioxaspiro[4,4]nonane

HRID 2286074Notes

Reaction equation

HRID 2286074 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][C:6]([CH:8]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:7])[CH3:2].Cl[CH2:29][C:30](=O)[CH2:31][CH2:32][O:33][CH2:34][CH3:35].[Cl-].C(O[CH2:41][CH2:42][C:43](=O)[CH2:44][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.[C:65](C=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)(=[O:71])[CH2:66][CH2:67][CH2:68][CH2:69]C.ClCC(=[O:100])CCCCC>>[OH:71][CH2:65][CH2:66][CH2:67][CH2:68][CH2:69][CH2:29][CH2:30][CH:31]1[CH:43]([CH:44]=[CH:8][C:6](=[O:7])[CH2:5][CH2:4][O:3][CH2:1][CH3:2])[CH2:42][CH2:41][C:32]21[O:100][CH2:35][CH2:34][O:33]2

Participants

6

Reactant 5

HCID 107619442-Heptanone, 1-(triphenylphosphoranylidene)-HCID 109536781-Chloroheptan-2-oneHCID 140688891-Chloro-4-ethoxybutan-2-oneHCID 205429223-EthoxypropionylmethylenetriphenylphosphoraneHCID 858551974-Ethoxy-2-oxobutyltriphenylphosphonium chloride

Product 1

HCID 570120136-(7-Hydroxyheptyl)-7-(5-ethoxy-3-oxopent-1-enyl)-1,4-dioxaspiro[4,4]nonane

Procedure

The 3-ethoxypropionylmethylenetriphenylphosphorane (m.p. 63°-65° C.), used as a starting material in the above preparation, was prepared from 1-chloro-4-ethoxybutan-2-one, via 4-ethoxy-2-oxobutyltriphenylphosphonium chloride (m.p. 157°-160° C.), by proceeding in a similar manner to that hereinbefore described in Example 3(i) for the preparation of hexanoylmethylenetriphenylphosphorane from 1-chloroheptan-2-one.

Sources & evidence

ORD record
ord-6d9972ad62774ff3b3098e38f5a04414
Source dataset
uspto-grants-1982_04
Patent number
US04325967

Reaction notes

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