Trifluoroacetic acid → HCID 22852538, compound

HRID 1654217Notes

Reaction equation

HRID 1654217 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([C@H:16]([O:18]C1CCCCO1)[CH3:17])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1.FC(F)(F)C(O)=O>C(O)C>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:25])([C@H:16]([OH:18])[CH3:17])[CH2:10][N:11]1[CH:15]=[CH:14][N:13]=[CH:12]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22852539HCID 22852539, compound

Product 1

HCID 22852538HCID 22852538, compoundYield 131.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (8.5 ml) was dissolved (3R)-2-(2,4-difluorophenyl)-1-(1-imidazolyl)-3-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)-2-butanol (1.7 g) followed by addition of trifluoroacetic acid (8.5 ml) at 0° C. After 10 minutes, the temperature was adjusted to 20° C. and the mixture was allowed to stand for 1 hour. The reaction mixture was then concentrated under reduced pressure and the residue was subjected to silica gel chromatography (2 cm×10 cm) using methanol-methylene chloride (1:9) as the eluent. The desired fraction was concentrated to give (3R)-2-(2,4-difluorophenyl)-1-(1-imidazolyl)-2,3-butanediol (1.7 g).

Workup

  1. customwas adjusted to 20° C.
  2. waitto stand for 1 hour
  3. concentrationThe reaction mixture was then concentrated under reduced pressure
  4. concentrationThe desired fraction was concentrated

Sources & evidence

ORD record
ord-6fa958e075f34af2b87ca3d70ae2c6a1
Source dataset
uspto-grants-1995_04
Patent number
US05405861

Reaction notes

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