Hydrochloric Acid → HCID 14516959, compound

HRID 1614440Notes

Reaction equation

HRID 1614440 reaction equation
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][CH:15]=1)[CH2:11][OH:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[F:20][C:21]([F:35])([F:34])[C:22]1([C:25]2[CH:30]=[CH:29][C:28]3[O:31][CH2:32][O:33][C:27]=3[CH:26]=2)[O:24][CH2:23]1.Cl>CN(C)C=O.O>[F:35][C:21]([F:20])([F:34])[C:22]([C:25]1[CH:30]=[CH:29][C:28]2[O:31][CH2:32][O:33][C:27]=2[CH:26]=1)([OH:24])[CH2:23][O:12][CH2:11][C:10]1[CH:13]=[CH:14][CH:15]=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 262953-Phenoxybenzyl alcoholHCID 14516958HCID 14516958, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 14516959HCID 14516959, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
22 °C

Procedure

3-Phenoxybenzyl alcohol (1.0 g) was added to a stirred suspension of sodium hydride (0.22 g, in the form of 0.44 g of a 50% dispersion in oil) in dry N,N-dimethylformamide (40 cm3), under an atmosphere of nitrogen. The mixture was stirred for a further 2 hours, during which time evolution of hydrogen occurred, and then added dropwise to the epoxide solution prepared in Stage 1. After a further 2 hours stirring at the ambient temperature (ca. 22° C.), the reaction mixture was poured into water, and the aqueous mixture acidified with dilute hydrochloric acid. This mixture was extracted with diethyl ether and the organic layer washed with water, dried over anhydrous magnesium sulphate, and concentrated by evaporation under reduced pressure to give an oil. The oil was purified by column chromatography on a silica gel support, eluting with n-hexane containing 15% by volume ethyl acetate, to give 1,1,1-trifluoro-2-(3,4-methylenedioxyphenyl)-3-(3-phenoxybenzyloxy)propan-2-ol (1.83 g), as a colourless oil.

Workup

  1. extractionThis mixture was extracted with diethyl ether
  2. washthe organic layer washed with water
  3. dry with materialdried over anhydrous magnesium sulphate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customto give an oil
  6. customThe oil was purified by column chromatography on a silica gel support
  7. washeluting with n-hexane containing 15% by volume ethyl acetate

Sources & evidence

ORD record
ord-bf20b7ddfb9946bf936a81d731505d1e
Source dataset
uspto-grants-1993_03
Patent number
US05196610

Reaction notes

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