Water → HCID 54263403, compound

HRID 543276Notes

Reaction equation

[H-].[Na+].O([C:10]1[CH:11]=[C:12]([CH2:17][CH2:18][CH2:19][C:20]([C:23]2[CH:28]=[CH:27]C(OCC)=CC=2)([CH3:22])C)[CH:13]=[CH:14][C:15]=1F)C1C=CC=CC=1.[Br:32][C:33]1[CH:34]=[C:35]([C:42]([CH3:47])([CH3:46])[CH2:43][CH:44]=O)[CH:36]=[CH:37][C:38]=1[O:39][CH2:40][CH3:41].[OH2:48]>COCCOC>[C:17]([C:18]1[CH:19]=[C:20]([CH:22]=[CH:44][CH2:43][C:42]([C:35]2[CH:36]=[CH:37][C:38]([O:39][CH2:40][CH3:41])=[C:33]([Br:32])[CH:34]=2)([CH3:47])[CH3:46])[CH:23]=[CH:28][CH:27]=1)(=[O:48])[C:12]1[CH:11]=[CH:10][CH:15]=[CH:14][CH:13]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To 5 ml of anhydrous dimethyl cellosolve was added 0.1 g of 60% sodium hydride, and thereinto 0.9 g of diethyl 3-benzoylbenzylphosphonate (prepared according to (1) of Synthesic Example 11) was added dropwise, and the mixture was stirred at 50° C. for 30 minutes. Then, a solution of 0.6 g of 3-(3-bromo-4-ethoxyphenyl)-3-methylbutanal in 2 ml of dimethyl cellosolve was added dropwise into the mixture, and stirred at 80° C. for one hour. After cooling, the reaction mixture was poured into water and extracted with benzene, and the benzene extract was washed with water and dried, and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: benzene) to give 0.7 g of the desired product.

Workup

stirringstirred at 80° C. for one hour
temperatureAfter cooling
extractionextracted with benzene
extractionthe benzene extract
washwas washed with water
customdried
customevaporated under reduced pressure
customThe residue was purified by column chromatography on silica gel (eluent: benzene)

Sources & evidence

ORD record: ord-d9731b7e17bf438792360a60b3759849
Source dataset: uspto-grants-1987_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04661501

Reaction notes

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