1,1,1-Trifluoro-2-propanol → HCID 86057409, compound

HRID 1820965Notes

Reaction equation

HRID 1820965 reaction equation
[F:1][C:2]([F:7])([F:6])[CH:3]([OH:5])[CH3:4].[H-].[Na+].F[C:11]1[CH:18]=[CH:17][C:16]([CH:19]=[O:20])=[CH:15][C:12]=1[C:13]#[N:14]>CN(C=O)C.CCOC(C)=O>[CH:19]([C:16]1[CH:17]=[CH:18][C:11]([O:5][CH:3]([CH3:4])[C:2]([F:7])([F:6])[F:1])=[C:12]([CH:15]=1)[C:13]#[N:14])=[O:20]

Participants

6

Reactant 3

HCID 97741,1,1-Trifluoro-2-propanolHCID 24758Sodium hydrideHCID 27695822-Fluoro-5-formylbenzonitrile

Product 1

HCID 86057409HCID 86057409, compoundYield 41.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.50 g (4.38 mmol) of 1,1,1-trifluoro-2-propanol in 15 mL of DMF at 0° C. was added 0.13 g (5.26 mmol) of sodium hydride (60% dispersion in mineral oil). After stirring for 10 min, 0.65 g (4.38 mmol) of 2-fluoro-5-formylbenzonitrile was added. The reaction mixture was gradually warmed up to rt and stirred overnight. The mixture was diluted with 20 mL of EtOAc and washed with brine (10 mL), H2O (3×10 mL), and brine (10 mL L). The organic layer was dried over MgSO4 and concentrated. Chromatography on a Biotage 40M cartridge using 4:1 v/v hexanes/EtOAc as the eluant gave 0.44 g of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.67 (d, J=6.4, 3H), 4.95 (m, 1H), 7.22 (d, J=8.9, 1H), 8.12 (dd, J=2.0, 6.7, 1H), 8.16 (s, 1H), 9.96 (s, 1H).

Workup

  1. stirringstirred overnight
  2. washwashed with brine (10 mL), H2O (3×10 mL), and brine (10 mL L)
  3. dry with materialThe organic layer was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-005cd6b4f4e1417098f86466a872814e
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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