Water → HCID 11648771, compound

HRID 1452704Notes

Reaction equation

HRID 1452704 reaction equation
[C:1]1([CH:7]([O:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]([OH:34])([C:30]([F:33])([F:32])[F:31])[C:26]([F:29])([F:28])[F:27])=[CH:21][CH:20]=2)[CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([CH:14]=[O:15])=[CH:12][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.CCO.[BH4-].[Na+].O>CCOC(C)=O>[F:27][C:26]([F:28])([F:29])[C:25]([C:22]1[CH:21]=[CH:20][C:19]([O:18][CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([CH2:14][OH:15])=[CH:12][CH:11]=2)=[CH:24][CH:23]=1)([OH:34])[C:30]([F:31])([F:33])[F:32]

Participants

6

Reactant 4

HCID 962WaterHCID 4311764Sodium borohydrideHCID 21873804Tetrahydrofuran ethanolHCID 87604907Rac 4-{2-phenyl-2-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-benzaldehyde

Product 1

HCID 11648771HCID 11648771, compoundYield 61.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

40 mg (0.08 mmol) of rac 4-{2-phenyl-2-[4-(2,2,2-trifluoro-1-hydroxy-1-trifluoromethyl-ethyl)-phenoxy]-ethoxy}-benzaldehyde in 2 mL of a mixture of THF/EtOH (1:1) were treated with 31 mg (0.8 mmol) of NaBH4 at 0° C. The mixture was stirred at room temperature, water and EtOAc were added, and the phases were separated. The inorganic phase was extracted with EtOAc, and the combined organic ones were washed with brine, dried (Na2SO4), filtered and evaporated. Column chromatography on ISOLUTE Flash NH2 with EtOAc yielded 24 mg (59%) of rac 1,1,1,3,3,3-hexafluoro-2-{4-[2-(4-hydroxymethyl-phenoxy)-1-phenyl-ethoxy]-phenyl}-propan-2-ol as a colorless oil, MS: 485 (M−H)−.

Workup

  1. customthe phases were separated
  2. extractionThe inorganic phase was extracted with EtOAc
  3. washthe combined organic ones were washed with brine
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-49cf6018a9e04fa38ff2a23893842baf
Source dataset
uspto-grants-2009_01
Patent number
US07473705B2

Reaction notes

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