Acetic Acid → HCID 58629923, compound

HRID 1391739Notes

Reaction equation

CC(O)=O.Cl[S:6]([C:9]1[CH:21]=[CH:20][C:12]([O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:11]([CH3:22])[CH:10]=1)(=O)=O.Cl[Si](Cl)(C)C.[F:28][C:29]([F:46])([F:45])[C:30]1[CH:35]=[CH:34][C:33]([C:36]2[CH:41]=[CH:40][CH:39]=[C:38]([CH:42](O)[CH3:43])[CH:37]=2)=[CH:32][CH:31]=1>CCOC(C)=O.[Zn]>[CH3:22][C:11]1[CH:10]=[C:9]([S:6][CH:42]([C:38]2[CH:37]=[C:36]([C:33]3[CH:34]=[CH:35][C:30]([C:29]([F:28])([F:45])[F:46])=[CH:31][CH:32]=3)[CH:41]=[CH:40][CH:39]=2)[CH3:43])[CH:21]=[CH:20][C:12]=1[O:13][CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]

Participants

Conditions

Temperature: 80 °C

Procedure

Zinc (229 mg, 3.50 mmol) was added to EtOAc (10 mL) followed by AcOH (115 μM, 2.00 mmol) and ethyl [4-(chlorosulfonyl)-2-methylphenoxy]acetate (293 mg, 1.00 mmol). After 2 hours, dichlorodimethylsilane (258 mg, 2.00 mmol) was added followed by 1-[4′-(trifluoromethyl)-3-biphenylyl]ethanol (266 mg, 1.00 mmol) and the mixture stirred for a further 1 hour and then heated at 80° C. for 5 hours. The mixture was then cooled, diluted with EtOAc and washed with saturated aqueous NaHCO3, saturated aqueous NH4Cl, water and brine, and then reduced. Purification by Biotage™ chromatography (silica) eluting with petrol:EtOAc (9:1) afforded the title compound as a colourless oil (238 mg).

Workup

temperatureThe mixture was then cooled
washwashed with saturated aqueous NaHCO3, saturated aqueous NH4Cl, water and brine
customPurification by Biotage™ chromatography (silica)
washeluting with petrol:EtOAc (9:1)

Sources & evidence

ORD record: ord-79411b63286245e3acdd06f653a78483
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07338960B2

Reaction notes

Loading…