Water → HCID 19909711, compound

HRID 1534454Notes

Reaction equation

HRID 1534454 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:15])[CH2:9][C:10]2[S:14][CH:13]=[N:12][CH:11]=2)=[CH:4][CH:3]=1.[CH2:16](O)[CH:17]([OH:19])[CH3:18].CS(O)(=O)=O.O>C1(C)C(C)=CC=CC=1.C(OCC)(=O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([CH2:9][C:10]3[S:14][CH:13]=[N:12][CH:11]=3)[O:19][CH:17]([CH3:18])[CH2:16][O:15]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1030Propylene GlycolHCID 6395Methanesulfonic AcidHCID 19909712HCID 19909712, compound

Product 1

HCID 19909711HCID 19909711, compound

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(4-fluorophenyl)-2-(5-thiazolyl)ethanone (0.75 g, 3.3 mmol) obtained by a process analogous to that described in Example 1, propane-1,2-diol (2 ml) and methanesulphonic acid (0.5 ml) in xylene (30 ml) was stirred at reflux under an atmosphere of nitrogen for 2 hours using a Dean and Stark apparatus and then cooled to room temperature. The reaction mixture was then poured into water, extracted with ethyl acetate and dried over magnesium sulphate. Evaporation of the solvent under reduced pressure afforded a dark brown oil and flash chromatography of this oil on a silica gel column using 2:8 (v/v) ethyl acetate: petroleum 60-80 yielded two enantiomeric pairs of 2-(4-fluorophenyl)-2-(thiazol-5-ylmethyl)-4-methyl-1,3-dioxolane as Sample A (2R,4R)(2S,4S) 0.17 g and Sample B (2R,4S)(2S,4R), 0.11 g, as oils.

Workup

  1. customobtained by a process analogous to
  2. temperatureat reflux under an atmosphere of nitrogen for 2 hours
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over magnesium sulphate
  5. customEvaporation of the solvent under reduced pressure
  6. customafforded a dark brown oil and flash chromatography of this oil on a silica gel column

Sources & evidence

ORD record
ord-3f98969229c84e6f930987dbc2e53a0e
Source dataset
uspto-grants-1992_02
Patent number
US05089512

Reaction notes

Loading…