1,4-Dioxaspiro[4.5]decan-8-one → Benzyl 2-(1,4-dioxaspiro[4,5]decan-8-ylidene)acetate

HRID 516869Notes

Reaction equation

C1(P(=[CH:20][C:21]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[O:31]1[C:35]2([CH2:40][CH2:39][C:38](=O)[CH2:37][CH2:36]2)[O:34][CH2:33][CH2:32]1>C1(C)C=CC=CC=1>[O:31]1[C:35]2([CH2:40][CH2:39][C:38](=[CH:20][C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:22])[CH2:37][CH2:36]2)[O:34][CH2:33][CH2:32]1

Participants

Conditions

Temperature: 95 °C

Procedure

Benzyl (triphenylphosphoranylidene)acetate (47.30 g, 115.2 mmol) was added to a solution of 1,4-dioxaspiro[4,5]decan-8-one (10.0 g, 64.02 mmol) in toluene (300 ml) at room temperature, and the mixture was stirred at 95° C. for 48 hr. The reaction mixture was allowed to cool to room temperature, and the solvent was removed by distillation under reduced pressure. The residue was diluted with ether and hexane, the resultant precipitate was removed by filtration, and the filtrate was concentrated. The residue was chromatographed on silica gel column (hexane:ethyl acetate=9:1) to give the title compound as a colorless oil (17.0 g, yield 92%).

Workup

temperatureto cool to room temperature
customthe solvent was removed by distillation under reduced pressure
additionThe residue was diluted with ether and hexane
customthe resultant precipitate was removed by filtration
concentrationthe filtrate was concentrated
customThe residue was chromatographed on silica gel column (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record: ord-1ef0c75488e643d7933a2c24f08c4872
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09115079B2

Reaction notes

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