Dicyclohexylcarbodiimide → HCID 20041584, compound

HRID 1762640Notes

Reaction equation

HRID 1762640 reaction equation
[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl.CN(C)C1C=CN=CC=1>[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH:11]2[CH2:13][CH2:12]2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].[CH3:1][C:2]1([CH3:17])[CH:4]([C:5]#[C:6][C:7]([O:9][CH3:10])=[O:8])[CH:3]1[C:14]([O-:16])=[O:15]

Participants

6

Reactant 2

HCID 10868DicyclohexylcarbodiimideHCID 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acid

Product 2

HCID 20041584HCID 20041584, compoundHCID 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

A solution of 21.6 g of the product of Step A in 75 ml of methylene chloride was added with stirring under an inert atmosphere to a solution of 19.9 g of (R, S) cyano-2-(6-phenoxypyridyl)-methanol in 75 ml of methylene chloride and then 1 g of 4-dimethylamino-pyridine was dissolved therein at 0° C. 21 g of dicyclohexylcarbodiimide were added to the mixture which was then stirred at room temperature for 4 hours and was then filtered. The filtrate was evaporated to dryness under reduced pressure at 40° C. and the residue was chromatographed over silica gel. Elution with a 7-3 cyclohexane-ethyl acetate mixture yielded 35.4 g of (R, S) cyano-2-(6-phenoxy-pyridyl)-methyl (1R, cis) 2,2-dimethyl-3-(3-methoxy-3-oxo-propynyl)-cyclopropane-carboxylate.

Workup

  1. customat 0° C
  2. filtrationwas then filtered
  3. customThe filtrate was evaporated to dryness under reduced pressure at 40° C.
  4. customthe residue was chromatographed over silica gel
  5. washElution with a 7-3 cyclohexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-25e23c8a7fdd45a48ed3848e1a2ba0fc
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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