Water → HCID 69220376, compound

HRID 1394610Notes

Reaction equation

[H-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH:8](P(OCC)(OCC)=O)[F:9])=[O:7].[CH:18]([C:20]1[S:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]3[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[CH:32]=[C:31]([CH:38]([CH3:40])[CH3:39])[C:30]=3[O:41][CH2:42][CH2:43][CH3:44])[C:22]=2[CH:21]=1)=O.O>CN(C=O)C>[CH2:4]([O:5][C:6](=[O:7])[C:8]([F:9])=[CH:18][C:20]1[S:24][C:23]2[CH:25]=[CH:26][CH:27]=[C:28]([C:29]3[CH:34]=[C:33]([CH:35]([CH3:37])[CH3:36])[CH:32]=[C:31]([CH:38]([CH3:39])[CH3:40])[C:30]=3[O:41][CH2:42][CH2:43][CH3:44])[C:22]=2[CH:21]=1)[CH3:3]

Participants

Conditions

Temperature: 40 °C

Procedure

To a slurry of 74 mg (1.54 mmol) of NaH (50% in mineral oil) in 3 mL of dry DMF was added 285.6 mg (1.27 mmol, 2.5 equivalents) of triethyl phosphonofluoroacetate (diluted in 1 mL of dry DMF) at 0° C. After the gas evolution has ceased, 0.51 mmol of 2-formyl-4-(2-n-propoxy-3,5-di-iso-propylphenyl)-benzo[b]thiophene diluted in 3 mL of dry DMF was added dropwise. The red mixture was slowly heated to 40° C. until complexion. After cooling, water was added and the solution was extracted 2 times with ethyl acetate. The organic layers were combined, washed with water and brine and dried over MgSO4. After evaporation of the solvents, the crude oil is purified over a short plug of silica gel (eluent: 95/5 hexane/ethyl acetate) to afford 2-fluoro-3-[4-(2-n-propoxy-3,5-di-iso-propylphenyl)-benzo[b]thien-2-yl]-prop-2-enoic acid ethyl ester.

Workup

additionwas added dropwise
temperatureAfter cooling
extractionthe solution was extracted 2 times with ethyl acetate
washwashed with water and brine
dry with materialdried over MgSO4
customAfter evaporation of the solvents
customthe crude oil is purified over a short plug of silica gel (eluent: 95/5 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-5c318c7cf9b4433b81e805897a857aab
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348359B2

Reaction notes

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