HCID 15132272, compound → HCID 15132273, compound

HRID 982407Notes

Reaction equation

HRID 982407 reaction equation
[C:1]1([CH:7]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH2:8][C:9](OCC)=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[C:1]1([CH:7]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([C:21]([F:22])([F:23])[F:24])=[CH:19][CH:20]=2)[CH2:8][CH2:9][OH:10])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 15132272HCID 15132272, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15132273HCID 15132273, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
22 °C

Procedure

A solution of 4.4 g (13.1 mmole) of ethyl 3-phenyl-4-(4-trifluoromethylphenyl)butanoate dissolved in 50 ml of tetrahydrofuran was added dropwise over a ten minute period to a 250 ml flask containing a 0° C. mixture of lithium aluminum hydride (745 mg, 19.6 mmole) in 50 ml of tetrahydrofuran. The resulting mixture was warmed to room temperature (22° C.), stirred at that temperature for about 2 hours, cooled to 0° C. again, and quenched by adding approximately 25 ml of water dropwise over a five minute period. The reaction mixture was acidified to a pH of about 1.0 using 6N hydrochloric acid and extracted with ethyl acetate. The organic extracts were combined, washed with water and a saturated brine solution, and finally dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure to provide 3.66 g of 3-phenyl-4-(4-trifluoromethylphenyl)butanol as a colorless oil. The compound was identified by N.M.R. analysis employing a 300 mHz instrument in CDCl3 ; δ=1.92 (multiplet, 2H); 2.97 (multiplet, 3H); 3.43 and 3.52 (multiplet, 2H); 7.08-7.53 (multiplet, 9H).

Workup

  1. additionwas added dropwise over a ten minute period to a 250 ml flask
  2. additioncontaining a 0° C.
  3. temperaturecooled to 0° C. again
  4. customquenched
  5. additionby adding approximately 25 ml of water dropwise over a five minute period
  6. extractionextracted with ethyl acetate
  7. washwashed with water
  8. dry with materiala saturated brine solution, and finally dried over anhydrous sodium sulfate
  9. customThe volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-52c63cb03959437bb91278b59c75970f
Source dataset
uspto-grants-1991_02
Patent number
US04996235

Reaction notes

Loading…