Potassium Sodium Tartrate → HCID 67364203, compound

HRID 217447Notes

Reaction equation

HRID 217447 reaction equation
[C:1]1([C:7]2[CH:8]=[C:9]([C:16](=[O:18])[CH3:17])[S:10][C:11]=2[C:12]([F:15])([F:14])[F:13])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1COCC1>[C:1]1([C:7]2[CH:8]=[C:9]([CH:16]([OH:18])[CH3:17])[S:10][C:11]=2[C:12]([F:13])([F:14])[F:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 9357Potassium Sodium TartrateHCID 14487Diisobutylaluminum hydrideHCID 27401391-[4-phenyl-5-(trifluoromethyl)-2-thienyl]ethan-1-one

Product 1

HCID 67364203HCID 67364203, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 1-[4-phenyl-5-(trifluoromethyl)-2-thienyl]ethanone (1.0 g) in THF (20 mL) was added dropwise DIBAL (0.99 M solution in toluene, 9.34 mL) at −78° C. The reaction mixture was warmed to 25° C. and stirred for 3 hours and a saturated aqueous Rochelle salt solution (50 mL) was added thereto, followed by extraction with EtOAc (50 mL) three times. The organic layer was washed with brine, dried over MgSO4, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=98:2 to 90:10) to obtain 1-[4-phenyl-5-(trifluoromethyl)-2-thienyl]ethanol (0.99 g) as a colorless liquid.

Workup

  1. extractionfollowed by extraction with EtOAc (50 mL) three times
  2. washThe organic layer was washed with brine
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (automatic purification device, hexane:EtOAc=98:2 to 90:10)

Sources & evidence

ORD record
ord-ca7b38777ee44d5d9594eda0edc0be3c
Source dataset
uspto-grants-2012_06
Patent number
US08193378B2

Reaction notes

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