2,2,2-Trifluoroethanol → HCID 18700398, compound

HRID 2288989Notes

Reaction equation

HRID 2288989 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][C:11]([S:13][CH3:14])=[N:10][C:9]=2[CH2:15][OH:16])=[CH:4][CH:3]=1.[F:17][C:18]([F:22])([F:21])[CH2:19]O.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O.C(P(CCCC)CCCC)CCC>C1(C)C=CC=CC=1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[O:12][C:11]([S:13][CH3:14])=[N:10][C:9]=2[CH2:15][O:16][CH2:19][C:18]([F:22])([F:21])[F:17])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 64092,2,2-TrifluoroethanolHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 18700449HCID 18700449, compound

Product 1

HCID 18700398HCID 18700398, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of [5-(4-fluoro-phenyl)-2-methylsulfanyl-oxazol-4-yl]-methanol (4.15 g; 17.34 mmol) in dry toluene (100 ml) was treated with 2,2,2-trifluoroethanol (12.63 ml; 173.4 mmol), 1,1'-(azodicarbonyl)dipiperidine (5.03 g; 19.94 mmol) and tributylphosphine (4.97 ml; 19.94 mmol) and stirred for 2 hours. The reaction mixture is partitioned between ethyl acetate (150 ml) and dilute sodium chloride solution (150 ml). The organic phase is washed with saturated brine (30 ml), dried over sodium sulfate and concentrated to dryness. Purification by flash chromatography on silica gel using an ethyl acetate/hexane gradient (2%-30%) afforded the product as a colorless residue (3.0 g; 49%). HNMR (CDCl3): 7.65 (m, 2H), 7.18 (t, 2H, J=8.7 Hz), 4.72 (s, 2H), 4.01 (qt, 2H, J=8.6 Hz), 2.73 (s, 3H). Mass spectrum: m/e calculated (MH+)=322; observed (MH+)=322.

Workup

  1. customThe reaction mixture is partitioned between ethyl acetate (150 ml) and dilute sodium chloride solution (150 ml)
  2. washThe organic phase is washed with saturated brine (30 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customPurification by flash chromatography on silica gel using an ethyl acetate/hexane gradient (2%-30%)
  6. customafforded the product as a colorless residue (3.0 g; 49%)

Sources & evidence

ORD record
ord-ffe6719093bd4067a5763a5cb9f1e98f
Source dataset
uspto-grants-2000_07
Patent number
US06090825

Reaction notes

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