Sodium Hydroxide → HCID 9837030, compound

HRID 1061263Notes

Reaction equation

HRID 1061263 reaction equation
[OH-].[Na+].Br[CH2:4][C@H:5]([C:7]1[N:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[S:10][CH:11]=1)[OH:6]>O1CCCC1.O>[O:6]1[CH2:4][C@@H:5]1[C:7]1[N:8]=[C:9]([C:12]([F:15])([F:14])[F:13])[S:10][CH:11]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 54321631HCID 54321631, compound

Product 1

HCID 9837030HCID 9837030, compoundYield 123.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide (5N, 11 mL) was added to a solution of (1S)-2-bromo-1-[2-(trifluoromethyl)-1,3-thiazole-4-yl]ethanol (which was obtained in Example 103) (1.52 g, 5.5 mmol) in tetrahydrofuran (6 mL). The mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with H2O (30 mL) and extracted with dichloromethane. The organic extracts were washed with H2O and brine, and dried over MgSO4. Evaporation and purification by flash chromatography (hexanes/dichloromethane 6/4) gave a clear oil (1.33 g, 74% yield); MS (ES) m/z: 196 (MH+); 1H NMR (400 MHz, CDCl3) δ 3.09 (m, 1H), 3.19 (m, 1H), 4.11 (m, 1H), 7.48 (s, 1H).

Workup

  1. extractionextracted with dichloromethane
  2. washThe organic extracts were washed with H2O and brine
  3. dry with materialdried over MgSO4
  4. customEvaporation and purification by flash chromatography (hexanes/dichloromethane 6/4)

Sources & evidence

ORD record
ord-02ddeda836b44a0c83512aec656ed6ea
Source dataset
uspto-grants-2003_02
Patent number
US06525202B2

Reaction notes

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