Water → HCID 14182038, compound

HRID 483746Notes

Reaction equation

HRID 483746 reaction equation
[H-].[Na+].[O:3]([C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=1)[CH2:13][OH:14])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[F:18][C:19]([F:35])([F:34])[C:20]1([C:23]2[CH:28]=[C:27]([F:29])[C:26]([O:30][CH2:31][CH3:32])=[C:25]([F:33])[CH:24]=2)[O:22][CH2:21]1.O>CN(C)C=O>[F:35][C:19]([F:18])([F:34])[C:20]([C:23]1[CH:24]=[C:25]([F:33])[C:26]([O:30][CH2:31][CH3:32])=[C:27]([F:29])[CH:28]=1)([OH:22])[CH2:21][O:14][CH2:13][C:12]1[CH:15]=[CH:16][CH:17]=[C:10]([O:3][C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 262953-Phenoxybenzyl alcoholHCID 14182037HCID 14182037, compound

Product 1

HCID 14182038HCID 14182038, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.48 g of a 50% dispersion in oil) was added to a stirred solution of m-phenoxybenzyl alcohol (2 g in dry N,N-dimethylformamide (20 cm3) under an atmosphere of dry nitrogen at the ambient temperature (ca 20° C.), and the mixture was stirred for 2 hours. The solution of (RS)-1,1,1-trifluoro-2-(3,5-difluoro-4-ethoxyphenyl) prop-2-ene oxide prepared in stage 1 was then added and the reaction mixture stirred for a further 2 hours. The mixture was then poured into water (100 cm3) and extracted with diethyl ether (2×100 cm3). The combined organic layers were dried over anhydrous sodium sulphate and evaporated under reduced pressure to give an oil which was purified by chromatography on a silica gel support, eluted with a mixture of n-hexane (8 parts by volume) containing ethyl acetate (1 part by volume), to give (RS)-1,1,1-trifluoro-2-(3,5-difluoro-4-ethoxyphenyl)-3-(3-phenoxybenzyloxy)propan-2-ol (0.7 g)--approximately 90% pure by gas liquid chromatographic analysis.

Workup

  1. stirringthe reaction mixture stirred for a further 2 hours
  2. extractionextracted with diethyl ether (2×100 cm3)
  3. dry with materialThe combined organic layers were dried over anhydrous sodium sulphate
  4. customevaporated under reduced pressure
  5. customto give an oil which
  6. customwas purified by chromatography on a silica gel support
  7. washeluted with a mixture of n-hexane (8 parts by volume)
  8. additioncontaining ethyl acetate (1 part by volume)

Sources & evidence

ORD record
ord-3cb32f48e7414f53b79b376689bb4563
Source dataset
uspto-grants-1993_07
Patent number
US05225607

Reaction notes

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