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

HRID 591079노트

반응식

HRID 591079 반응식
[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

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e8f97823ec0341a18c1b25fdf60985a2
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09238026B2

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