HCID 23614501, compound → HCID 22647464, compound

HRID 1767929Notes

Reaction equation

HRID 1767929 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[S:5][C:6]=1[CH2:7][C:8](O)=[O:9]>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[CH:12]=2)[S:5][C:6]=1[CH2:7][CH2:8][OH:9]

Participants

3

Reactant 1

HCID 23614501HCID 23614501, compound

Product 1

HCID 22647464HCID 22647464, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of [4-methyl-2-(3-trifluoromethyl-phenyl)-thiazol-5-yl]-acetic acid (430 mg, 1.4 mmol) in tetrahydrofuran (6 ml) was treated at 0° C. with a 1 M solution of BH3*THF in tetrahydrofuran (3.6 ml, 3.6 mmol). The cooling bath was removed and the reaction mixture stirred at ambient temperature for 16 h. Careful quenching with MeOH and ice water, twofold extraction with AcOEt, washing with ice water/brine 1/1, drying over magnesium sulfate, and evaporation of the solvent left a crude product which was refluxed for 30 min in MeOH to liberate quantitatively the free alcohol. The solvent was evaporated in vacuo and the residue was purified by column chromatography (silica gel, n-heptane/ethyl acetate) to yield 230 mg (0.8 mmol, 56%) of the title compound as yellow oil.

Workup

  1. customThe cooling bath was removed
  2. customCareful quenching with MeOH and ice water, twofold extraction with AcOEt
  3. washwashing with ice water/brine 1/1
  4. dry with materialdrying over magnesium sulfate, and evaporation of the solvent
  5. waitleft a crude product which
  6. temperaturewas refluxed for 30 min in MeOH
  7. customThe solvent was evaporated in vacuo
  8. customthe residue was purified by column chromatography (silica gel, n-heptane/ethyl acetate)

Sources & evidence

ORD record
ord-cf8f0a6e3a524dc38dd6cff37f1d2920
Source dataset
uspto-grants-2007_06
Patent number
US07235572B2

Reaction notes

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