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Water → 3,3-Dimethylspiro-(cyclopropane-1,1'-indene)2-carboxylic acid alpha-cyano-3-phenoxy-4-fluoro-benzyl ester

HRID 2058453
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HRID 2058453 반응식
[O:1]([C:8]1[CH:9]=[C:10]([CH:13]=[CH:14][C:15]=1[F:16])[CH:11]=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:17][C:18]1([CH3:32])[C:20]2([C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)[CH:19]1[C:29](Cl)=[O:30].[C-:33]#[N:34].[Na+].O>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1.CCCCCC>[C:33]([CH:11]([O:12][C:29]([CH:19]1[C:20]2([C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=[CH:21]2)[C:18]1([CH3:32])[CH3:17])=[O:30])[C:10]1[CH:13]=[CH:14][C:15]([F:16])=[C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH:9]=1)#[N:34]
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참가 물질

8

반응물 4

HCID 962WaterHCID 8929Sodium CyanideHCID 1084583,3-Dimethylspiro(cyclopropane-1,1'-(1H)indene)-2-carbonyl chlorideHCID 1100684-Fluoro-3-phenoxybenzaldehyde

생성물 1

HCID 127745623,3-Dimethylspiro-(cyclopropane-1,1'-indene)2-carboxylic acid alpha-cyano-3-phenoxy-4-fluoro-benzyl ester수율 79.5%

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매
HCID 1140Toluene용매
HCID 8058Hexane용매

실험 절차

5 g (0.0232 mol) of 3-phenoxy-4-fluoro-benzaldehyde and 5.4 g (0.0232 mol) of 3,3-dimethylspiro-(cyclopropane-1,1'-indene)-2-carboxylic acid chloride were together added dropwise to a mixture of 1.8 g of sodium cyanide, 2.7 ml of water, 100 ml of n-hexane and 0.5 g of tetrabutylammonium bromide at 20°-25° C., while stirring, and the mixture was subsequently stirred at 20°-25° C. for 4 hours. 300 ml of toluene were then added to the reaction mixture and the mixture was extracted twice by shaking with 300 ml of water each time. The organic phase was separated off and dried over magnesium sulphate and the solvent was distilled off under a water-pump vacuum. Last residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg. 8.1 g (79.5% of theory) of 3,3-dimethylspiro-(cyclopropane-1,1'-indene)2-carboxylic acid α-cyano-3-phenoxy-4-fluoro-benzyl ester were obtained as a viscous oil. The structure was confirmed by the 1H-NMR spectrum.

후처리

  1. stirringthe mixture was subsequently stirred at 20°-25° C. for 4 hours
  2. extractionthe mixture was extracted twice
  3. stirringby shaking with 300 ml of water each time
  4. customThe organic phase was separated off
  5. dry with materialdried over magnesium sulphate
  6. distillationthe solvent was distilled off under a water-pump vacuum
  7. customLast residues of solvent were removed by brief incipient distillation at a bath temperature of 60° C./1 mm Hg

출처 및 근거

ORD 기록
ord-ccf022d4bdb944c3a0f84f0e9f69b43b
출처 데이터셋
uspto-grants-1982_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04317834

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