Diisopropylamine → HCID 14347486, compound

HRID 1110492Notes

Reaction equation

HRID 1110492 reaction equation
[CH:1]([NH:4]C(C)C)(C)[CH3:2].C([Li])CCC.[F:13][C:14]([F:34])([F:33])[C:15]1[CH:32]=[CH:31][CH:30]=[CH:29][C:16]=1[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:28])([F:27])[F:26])=[O:18]>O1CCCC1.CCCCCC>[OH:18][C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]([F:26])([F:27])[F:28])([C:16]1[CH:29]=[CH:30][CH:31]=[CH:32][C:15]=1[C:14]([F:33])([F:34])[F:13])[CH2:2][C:1]#[N:4]

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 12434983Bis[2-(trifluoromethyl)phenyl]methanoneHCID 178418339Butyllithium

Product 1

HCID 14347486HCID 14347486, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

A stirred solution of diisopropylamine (4.02 mL) in dry tetrahydrofurane (30 mL) under argon was treated dropwise with 1.6M n-butyl lithium in hexane (18 mL). The reaction was kept at -5° C. during the addition and for 15 minutes thereafter, then it was cooled to -78° C. and a solution of 2,2'-bis(trifluoromethyl)benzophenone (8.0 g) in tetrahydrofurane was added at such a rate that the reaction temperature did not exceed -65° C. The mixture was stirred at -78° C. for 10 minutes, then it was allowed to slowly equilibrate to room temperature over 30 minutes. After the solvents were removed under reduced pressure, the residue was treated with water (100 mL) and the resulting solid was filtered off, washed with water and dried. Crystallization of the solid from dichloromethanehexane furnished 7.72 g of 3-hydroxy-3,3-bis[2-(trifluoromethyl)phenyl]-propanenitrile, mp 168°-170° C. A sample was recrystallized from the same solvent system to give the analytical specimen, mp 171°-172° C. Anal. Calculated for C17H11F6NO: 56.83: H, 3.08: F, 31.73: N, 3.80. Found: C. 56.87; H, 2.81: F, 31.88: N, 4.14.

Workup

  1. additionThe reaction was kept at -5° C. during the addition and for 15 minutes
  2. customdid not exceed -65° C
  3. customslowly equilibrate to room temperature
  4. customover 30 minutes
  5. customAfter the solvents were removed under reduced pressure
  6. additionthe residue was treated with water (100 mL)
  7. filtrationthe resulting solid was filtered off
  8. washwashed with water
  9. customdried
  10. customCrystallization of the solid from dichloromethanehexane

Sources & evidence

ORD record
ord-a8cba5c66a504b14a2368e093a2e7ad0
Source dataset
uspto-grants-1990_12
Patent number
US04975438

Reaction notes

Loading…