Water → 7-[2-(3-Hydroxy-3-methyloct-1-enyl)-5-oxocyclopentyl]heptanol
Reaction equation
[OH:1][C:2]([CH3:31])([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:3]=[CH:4][CH:5]1[CH2:13][CH2:12][C:7]2(OCC[O:8]2)[CH:6]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][O:21][Si](C)(C)C.O.C1(C)C=CC=CC=1>C(O)(=O)C.O1CCOCC1>[OH:1][C:2]([CH3:31])([CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH:3]=[CH:4][CH:5]1[CH2:13][CH2:12][C:7](=[O:8])[CH:6]1[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][OH:21]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
7-(3-Hydroxy-3-methyloct-1-enyl)-6-(7-trimethylsiloxyheptyl)-1,4-dioxaspiro[4,4]nonane [0.5 g; prepared as hereinbefore described in Example 3(iii)], water (10 ml.) and glacial acetic acid (20 ml.) were left to stand together at room temperature for 6 hours. The solution was then evaporated in vacuo at a temperature below 50° C. Ethyl acetate (150 ml.) was added to the residue and the resulting solution was washed with water until the pH of the washings was 5, dried over sodium sulphate, and evaporated to give a crude product (0.37 g.). The crude product was subjected to preparative thin layer chromatrography on silica gel, using a mixture of toluene, dioxan and acetic acid (65:15:1 by volume) as eluant, eluting twice, to give 7-[2-(3-hydroxy-3-methyloct-1-enyl)-5-oxocyclopentyl]heptanol (0.12 g.).
Workup
- customThe solution was then evaporated in vacuo at a temperature below 50° C
- additionEthyl acetate (150 ml.) was added to the residue
- washthe resulting solution was washed with water until the pH of the washings
- dry with materialdried over sodium sulphate
- customevaporated
- customto give a crude product (0.37 g.)
- washeluting twice
Sources & evidence
- ORD record
- ord-785825bec66d4030909719347420439b
- Source dataset
- uspto-grants-1982_04
- Patent number
- US04325967
Reaction notes
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