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

HRID 591079ノート

反応式

HRID 591079 の反応式
[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

参加物

5

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e8f97823ec0341a18c1b25fdf60985a2
出典データセット
uspto-grants-2016_01
特許番号
US09238026B2

反応ノート

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