Sodium ethoxide → HCID 10252527, compound

HRID 2105982Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]2([C:13]([F:16])([F:15])[F:14])[CH2:12][O:11]2)[CH:7]=1.[OH:21][C:22]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=2)[N:25]=[CH:24][CH:23]=1.[O-]CC.[Na+]>CCO.CCOC(C)=O.C(O)(=O)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:19][CH3:20])=[C:6]([C:8]([CH3:18])([CH3:17])[CH2:9][C:10]([OH:11])([C:13]([F:16])([F:15])[F:14])[CH2:12][N:25]2[C:26]3[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:22](=[O:21])[CH:23]=[CH:24]2)[CH:7]=1

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of 2-[2-(5-fluoro-2-methoxyphenyl)-2-methylpropyl]-2-trifluoromethyloxirane (see Example 1) (0.21 g) and 4-hydroxyquinoline (0.105 g) and sodium ethoxide (21 wt. % in EtOH) in 4 mL anhydrous EtOH was heated at 85° C. for 6 hours, cooled to room temperature, diluted with EtOAc and acetic acid, washed with water and brine, and dried over magnesium sulfate. Removal of the volatiles in vacuo provided a residue which was purified with flash silica gel using EtOAc as the eluent. Concentration in vacuo of the product-rich fractions provided the title compound, m.p. 170° C.-172° C.

Workup

temperaturecooled to room temperature
washwashed with water and brine
dry with materialdried over magnesium sulfate
customRemoval of the volatiles in vacuo
customprovided a residue which
customwas purified with flash silica gel
concentrationConcentration in vacuo of the product-rich fractions

Sources & evidence

ORD record: ord-dd17af597d58403eaaaa0468710d2783
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07579469B2

Reaction notes

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