Water → HCID 86749907, compound

HRID 864494Notes

Reaction equation

HRID 864494 reaction equation
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH2:15][CH:16]([OH:30])[CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[H-].[Na+].Br[CH2:36][C:37]([O:39][CH3:40])=[O:38].O>O1CCCC1.CN(C)C=O.C(OCC)(=O)C>[F:1][C:2]([F:31])([F:32])[C:3]1[CH:4]=[C:5]([CH2:13][O:14][CH2:15][CH:16]([O:30][CH2:36][C:37]([O:39][CH3:40])=[O:38])[CH:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:6]=[C:7]([C:9]([F:11])([F:12])[F:10])[CH:8]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 9933653HCID 9933653, compound

Product 1

HCID 86749907HCID 86749907, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a cooled solution (0° C.) of 1-(3,5-bis(trifluoromethyl) phenyl)methyloxy-3,3-diphenyl-2-hydroxypropane (Example 1; 0.49 g) in a mixture of tetrahydrofuran (4 ml) and dimethylformamide (1 ml) was added 80% sodium hydride (0.039 g; suspension in oil). After 0.5 hours methyl bromoacetate (0.121 ml) was added and the solution stirred at room temperature for 16 hours. Water (0 ml) and ethyl acetate (50 ml) were added and the organic phase washed with water (5 times), saturated brine and dried (MgSO4). After removal of the solvent in vacuo the residue was purified by silica gel chromatography (eluting with 10% ethyl acetate in hexane) to give 1-((3,5-bis(trifluoromethyl)phenyl)methyloxy)-2-(carbomethoxy) methyloxy-3,3-diphenylpropane m/e CI+ =544 (M+NH4+).

Workup

  1. washthe organic phase washed with water (5 times), saturated brine
  2. dry with materialdried (MgSO4)
  3. customAfter removal of the solvent in vacuo the residue
  4. customwas purified by silica gel chromatography (eluting with 10% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-bb91baf124ac48b3a1fefb2d11f04b58
Source dataset
uspto-grants-1996_10
Patent number
US05563161

Reaction notes

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