Water → ethyl 2-[1-benzyl-5-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(trifluoromethyl)-1H-pyrazol-4-yl]-2-hydroxyacetate

HRID 591079Notes

Reaction equation

HRID 591079 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][CH2:21][CH2:20][C:19]=3[CH:24]=2)=[C:13]([C:25](=[O:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:12]([C:32]([F:35])([F:34])[F:33])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.O>CO>[CH2:3]([N:10]1[C:14]([C:15]2[CH:16]=[CH:17][C:18]3[O:23][CH2:22][CH2:21][CH2:20][C:19]=3[CH:24]=2)=[C:13]([CH:25]([OH:31])[C:26]([O:28][CH2:29][CH3:30])=[O:27])[C:12]([C:32]([F:33])([F:35])[F:34])=[N:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 70855456ethyl 2-[1-benzyl-5-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(trifluoromethyl)-1H-pyrazol-4-yl]-2-oxoacetate

Product 1

HCID 70855451ethyl 2-[1-benzyl-5-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(trifluoromethyl)-1H-pyrazol-4-yl]-2-hydroxyacetateYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Under a nitrogen atmosphere, sodium borohydride (6.44 mg, 0.17 mmol) was added portionwise to a solution of ethyl 2-[1-benzyl-5-(3,4-dihydro-2H-1-benzopyran-6-yl)-3-(trifluoromethyl)-1H-pyrazol-4-yl]-2-oxoacetate (49e) (78 mg, 0.17 mmol) in anhydrous methanol (2 mL). After 2 hours stirring, water was added (3 mL). The methanol was removed under reduced pressure, and the aqueous layer was extracted with ethyl acetate (2×5 mL). The organic layer was successively washed with water (3 mL) and brine (3 mL), before being dried over sodium sulfate and concentrated in vacuo to provide the desired alcohol (49f) (70 mg, 0.17 mmol, 89%) which was used without further purification.

Workup

  1. customThe methanol was removed under reduced pressure
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×5 mL)
  3. washThe organic layer was successively washed with water (3 mL) and brine (3 mL)
  4. dry with materialbefore being dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e8f97823ec0341a18c1b25fdf60985a2
Source dataset
uspto-grants-2016_01
Patent number
US09238026B2

Reaction notes

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