Water → HCID 77886384, compound

HRID 436877Notes

Reaction equation

[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][C:10]2([O:17][CH2:16][CH2:15][O:14]2)[CH2:11][CH2:12][CH3:13])C=CC=CC=1.[CH3:30][O:31][C:32]([CH3:40])([CH3:39])[CH2:33][CH2:34][CH2:35][C:36](=O)[CH3:37].O>CN(C)C=O>[CH2:16]1[CH2:15][O:14][C:10]([CH2:11][CH2:12][CH:13]=[C:36]([CH3:37])[CH2:35][CH2:34][CH2:33][C:32]([O:31][CH3:30])([CH3:40])[CH3:39])([CH3:9])[O:17]1

Participants

Conditions

Temperature: 0 °C

Procedure

8.15 g of potassium tert.-butylate were added to a solution of 38 g of triphenyl 2,2-ethylenedioxy-pentyl phosphonium bromide in 400 ml of dimethylformamide cooled to 0° C. and then 12.75 g of 6-methoxy-6-methyl-2-heptanone were added. The mixture was stirred for 4 hours at 0° C. and was then poured into water. The mixture was extracted with petroleum ether (b.p.= 40°-75° C.) and the extracts were washed with water, dried over sodium sulfate and evaporated to dryness. The yellow oil was chromatographed over silica and was eluted with a 8-2 benzene-ethyl acetate mixture to obtain 9.15 g of 2,2-ethylenedioxy-10-methoxy-6,10-dimethyl-5-undecene in the form of a colorless oil which was a mixture of the E and Z isomers with respect to the double bond in the 5-position. A supplementary chromatography under pressure and elution with a 9-1 benzene-ethyl acetate mixture gave a separation of the E and Z isomers.

Workup

extractionThe mixture was extracted with petroleum ether (b.p.= 40°-75° C.)
washthe extracts were washed with water
dry with materialdried over sodium sulfate
customevaporated to dryness
customThe yellow oil was chromatographed over silica
washwas eluted with a 8-2 benzene-ethyl acetate mixture

Sources & evidence

ORD record: ord-2c1f00dccba246528533833ce4777a26
Source dataset: uspto-grants-1977_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04028386

Reaction notes

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