Trifluoroacetic acid → HCID 19433125, compound

HRID 1736494Notes

Reaction equation

HRID 1736494 reaction equation
[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([OH:21])[CH2:20][CH2:19][CH2:18][S:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.F[C:23](F)(F)C(O)=O>CO>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([C:15]3([O:21][CH3:23])[CH2:20][CH2:19][CH2:18][S:17][CH2:16]3)[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 19433119HCID 19433119, compound

Product 1

HCID 19433125HCID 19433125, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-hydroxy-3,4,5,6-tetrahydro-2H-thiopyran (2 g; which is prepared as described in Example 7) methanol (175 mL) is treated with trifluoroacetic acid (0.5 mL) and the mixture is allowed to stand at room temperature overnight. The mixture is concentrated in vacuo, and it is then treated with diethyl ether (175 mL) and washed with saturated aqueous sodium bicarbonate solution (25 mL) and water (25 mL) and dried over magnesium sulphate. The solvent is removed and the resulting oily residue is subjected to flash chromatography on silica gel, using a mixture of pentane and ethyl acetate (9:1 v/v) as eluent, to give 3-(3-cyclopentyloxy-4-methoxyphenyl)-3-methoxy-3,4,5,6-tetrahydro-2H-thiopyran (1.16 g), in the form of a colorless oil.

Workup

  1. concentrationThe mixture is concentrated in vacuo, and it
  2. additionis then treated with diethyl ether (175 mL)
  3. washwashed with saturated aqueous sodium bicarbonate solution (25 mL) and water (25 mL)
  4. dry with materialdried over magnesium sulphate
  5. customThe solvent is removed
  6. additiona mixture of pentane and ethyl acetate (9:1 v/v) as eluent

Sources & evidence

ORD record
ord-12e27711e8bf4ba4bfed80eca01b8c73
Source dataset
uspto-grants-1996_07
Patent number
US05541219

Reaction notes

Loading…