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6-Phenoxy-2-pyridinemethanol → (6-Phenoxy-2-pyridinyl)methyl 2,2-dimethyl-3-((isobutoxyimino)methyl)cyclopropanecarboxylate

HRID 1380907
Notes
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Reaction equation

HRID 1380907 reaction equation
[CH3:1][C:2]1([CH3:15])[C@@H:4]([CH:5]=[N:6][O:7][CH2:8][CH:9]([CH3:11])[CH3:10])[C@H:3]1[C:12]([OH:14])=[O:13].[O:16]([C:23]1[N:28]=[C:27]([CH2:29]O)[CH:26]=[CH:25][CH:24]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C1C=CN=CC=1.C(Cl)Cl.CCCCCC>[CH3:15][C:2]1([CH3:1])[CH:4]([CH:5]=[N:6][O:7][CH2:8][CH:9]([CH3:11])[CH3:10])[CH:3]1[C:12]([O:14][CH2:29][C:27]1[CH:26]=[CH:25][CH:24]=[C:23]([O:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:28]=1)=[O:13]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 2

HCID 128791556-Phenoxy-2-pyridinemethanolHCID 53776025(1R,cis)-2,2-dimethyl-3-((isobutoxyimino)methyl)cyclopropanecarboxylic acid

Product 1

HCID 54522051(6-Phenoxy-2-pyridinyl)methyl 2,2-dimethyl-3-((isobutoxyimino)methyl)cyclopropanecarboxylateYield 71.7%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalyst
HCID 6344
Dichloromethane
Solvent
HCID 8058HexaneSolvent

Procedure

To a stirred solution of 0.75 g of (1R,cis)-2,2-dimethyl-3-((isobutoxyimino)methyl)cyclopropanecarboxylic acid, 0.71 g of 6-phenoxy-2-pyridinemethanol and a catalytic amount of 4-dimethylaminopyridine in 40 ml of methylene chloride under argon was added as one portion 1.19 g of N,N-dicyclohexylcarbodiimide. The reaction mixture was stirred at ambient temperature overnight, then diluted with an equal volume of hexane, filtered and stripped. The resulting oil was dissolved in hexane, filtered, washed with dilute potassium carbonate solution, dried and stripped. The crude product was chromatographed using 20% diethyl ether in hexane as eluent to yield 1.0 g of the desired product.

Workup

  1. filtrationfiltered
  2. dissolutionThe resulting oil was dissolved in hexane
  3. filtrationfiltered
  4. washwashed with dilute potassium carbonate solution
  5. customdried
  6. customThe crude product was chromatographed

Sources & evidence

ORD record
ord-0050fab3a16d494e84cb845bf180fefb
Source dataset
uspto-grants-1986_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04584304

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes