2,2,2-Trifluoroethanol → HCID 19047034, compound

HRID 1780584Notes

Reaction equation

HRID 1780584 reaction equation
[Na].[CH2:2]([OH:7])[C:3]([F:6])([F:5])[F:4].[CH3:8][C:9]([CH3:31])([CH3:30])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=1[C:20]1[CH:25]=[CH:24][N:23]=[C:22](S(C)(=O)=O)[N:21]=1)=[O:11]>O1CCCC1>[CH3:8][C:9]([CH3:31])([CH3:30])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][C:14]=1[C:20]1[CH:25]=[CH:24][N:23]=[C:22]([O:7][CH2:2][C:3]([F:6])([F:5])[F:4])[N:21]=1)=[O:11]

Participants

5

Reactant 3

HCID 64092,2,2-TrifluoroethanolHCID 5360545Sodium2×HCID 19047042HCID 19047042, compound

Product 1

HCID 19047034HCID 19047034, compoundYield 89.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.10 g sodium metal was covered under nitrogen with 15 mL anhydrous tetrahydrofuran and 1 g trifluoroethanol was added dropwise with stirring. Stirring was continued for 1.5 h at which time the sodium was completely reacted. A solution of 0.4 g 2,2-dimethyl-N-[4-methyl-2-[2-(methylsulfonyl)-4-pyrimidinyl]phenyl]propanamide was added via syringe and stirring continued overnight under nitrogen. The reaction mixture was quenched with water and extracted with ether. The organic extracts were washed with water and brine, dried over magnesium sulfate, filtered, and evaporated to dryness. The crude product was purified by chromatography on silica gel using 40:1 chlorobutane/ethyl acetate mixture as eluent to yield 0.38 g of the title compound as white crystals melting at 126°-128° C. 1H NMR (CDCl3): δ 1.28 (s,9H), 2.40 (s,3H), 4.85 (q,2H), 7.30-8.6 (5H), 11.9(s,1H,NH).

Workup

  1. additionwas added dropwise
  2. stirringStirring
  3. stirringstirring continued overnight under nitrogen
  4. customThe reaction mixture was quenched with water
  5. extractionextracted with ether
  6. washThe organic extracts were washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated to dryness
  10. customThe crude product was purified by chromatography on silica gel using 40:1 chlorobutane/ethyl acetate mixture as eluent

Sources & evidence

ORD record
ord-d54c4e186eb54a2d8a3ee48b9fef723e
Source dataset
uspto-grants-1997_05
Patent number
US05631206

Reaction notes

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