Sodium Hydroxide → HCID 69184067, compound

HRID 513181Notes

Reaction equation

HRID 513181 reaction equation
[F:1][C:2]([F:21])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[C:13]([C:15](OCC)=[O:16])[N:14]=2)=[CH:6][CH:5]=1.[Li+].[BH4-].[OH-].[Na+]>CC1OCCC1.C1COCC1.CCOC(C)=O>[F:21][C:2]([F:1])([F:20])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[S:11][CH:12]=[C:13]([CH2:15][OH:16])[N:14]=2)=[CH:6][CH:5]=1

Participants

7

Reactant 3

HCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 59840616HCID 59840616, compound

Product 1

HCID 69184067HCID 69184067, compoundYield 97.3%

Reagents, catalysts & solvents 3

HCID 73012-MethyltetrahydrofuranSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2-[4-(trifluoromethoxy)phenyl]-1,3-thiazole-4-carboxylate (71 mg, 0.224 mmol) in 2-MeTHF (1 mL) was added 2M LiBH4 (0.224 mL, 0.448 mmol) in THF slowly at RT. After 90 min the mixture was quenched by the addition of 2M NaOH (0.6 mL, 1.200 mmole). The mixture was stirred for 4 hr then diluted with EtOAc, filtered through a pad of Celite and concentrated to give the title compound (60 mg, 97%). 1H NMR (400 MHz, CDCl3): δ 8.00-7.96 (m, 2 H); 7.31-7.25 (m, 2 H); 7.21 (s, 1 H); 4.84 (d, J=5.6 Hz, 2 H); 2.29-2.22 (m, 1 H).

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-da15299508d1461cbed3847fa7d1de1d
Source dataset
uspto-grants-2015_08
Patent number
US09102673B2

Reaction notes

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