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Sodium Hydroxide → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanal

HRID 218156
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HRID 218156 반응식
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:18]([CH3:22])([CH3:21])[CH2:19][OH:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH-].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([CH:17]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:18]([CH3:22])([CH3:21])[CH:19]=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1
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5

반응물 3

HCID 14798Sodium HydroxideHCID 159087TriacetoxyperiodinaneHCID 687058683-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropan-1-ol

생성물 1

HCID 592510413-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanal수율 79%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a stirred solution of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropan-1-ol (1.3 g, 3.5 mmol) in CH2Cl2 (150 mL) was added Dess-Martin periodinane (2.12 g, 5.0 mmol) portionwise at RT under nitrogen. After stirring at RT for 24 hr, the mixture was poured into a 1N sodium hydroxide solution (100 mL), extracted with CH2Cl2 (100 mL), dried (Na2SO4) and concentrated. The crude residue was purified over silica gel eluting with EtOAc/hexanes (1:3) to give 1.03 g (79% yield) of 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-2,2-dimethyl-3-phenylpropanal, the NMR spectrum of which was consistent with the desired structure.

후처리

  1. extractionextracted with CH2Cl2 (100 mL)
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customThe crude residue was purified over silica gel eluting with EtOAc/hexanes (1:3)

출처 및 근거

ORD 기록
ord-b96b445d73664f88b8e60e33c732afba
출처 데이터셋
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08198311B2

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