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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
Notes
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Reaction equation

HRID 2058453 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents

3
HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolventHCID 8058HexaneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-ccf022d4bdb944c3a0f84f0e9f69b43b
Source dataset
uspto-grants-1982_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04317834

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes