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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
ノート
印刷プレビュー

反応式

HRID 2058453 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 74236
Tetrabutylammonium Bromide
触媒
HCID 1140Toluene溶媒
HCID 8058Hexane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-ccf022d4bdb944c3a0f84f0e9f69b43b
出典データセット
uspto-grants-1982_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04317834

反応ノート

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