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Pyridine → (S)-alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(methoxycarbonyl)-ethenyl]-cyclopropane-carboxylate

HRID 1995152
Notes
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Reaction equation

HRID 1995152 reaction equation
[CH3:1][C:2]1([CH3:14])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH3:10])=[O:8])[C@H:3]1[C:11]([OH:13])=[O:12].N1C=CC=CC=1.[C:21]([C@@H:23](O)[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:25]=1)#[N:22]>C(Cl)Cl>[CH3:1][C:2]1([CH3:14])[C@@H:4](/[CH:5]=[CH:6]\[C:7]([O:9][CH3:10])=[O:8])[C@H:3]1[C:11]([O:13][C@H:23]([C:21]#[N:22])[C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([O:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:25]=1)=[O:12]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1049PyridineHCID 9837437(2S)-2-hydroxy-2-(3-phenoxyphenyl)acetonitrileHCID 12807748(1R, cis)2,2-dimethyl-3-[(Z)-2-(methoxy carbonyl)-ethenyl]-cyclopropane-carboxylic acid

Product 1

HCID 13105998(S)-alpha-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(methoxycarbonyl)-ethenyl]-cyclopropane-carboxylateYield 73.3%

Reagents, catalysts & solvents 1

HCID 6344
Dichloromethane
Solvent

Procedure

7 g of the product of Step C, 7.3 g of dicyclohexylcarbodiiumide and 3 ml of pyridine were added to 50 ml of methylene chloride and after the addition of 8 g of (S)α-cyano-3-phenoxy-benzyl alcohol, the mixture was stirred at room temperature for 16 hours. The mixture was filtered and the filtrate was evaporated to dryness under reduced pressure. The 20 g of residue were crystallized from isopropyl ether to obtain 10.5 g of (S)-α-cyano-3-phenoxy-benzyl (1R,cis) 2,2-dimethyl-3-[Z-2-(methoxycarbonyl)-ethenyl]-cyclopropane-carboxylate melting at 98° C.

Workup

  1. filtrationThe mixture was filtered
  2. customthe filtrate was evaporated to dryness under reduced pressure
  3. customThe 20 g of residue were crystallized from isopropyl ether

Sources & evidence

ORD record
ord-24e47a4ddf88495baa74c7aa5fdebafc
Source dataset
uspto-grants-1983_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04402972

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes