Allyl Alcohol → 2,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acid

HRID 1762642Notes

Reaction equation

HRID 1762642 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].CC1(C)C(C=CC(O)=O)C1C([O-])=O.C(O)C=C>>[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]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH:11]=[CH2:12])=[O:8])[CH:3]1[C:14]([O-:16])=[O:15]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acidHCID 735091832,2-Dimethyl-3-(3-hydroxy-3-oxo-1-propenyl)-cyclopropane-carboxylate

Product 2

HCID 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acidHCID 736755802,2-Dimethyl-3-(3-allyloxy-3-oxo-1-propenyl)-cyclopropane-carboxylate

Procedure

Using the procedure of Example 84, 2.1 g of (R, S) cyano-2-(6-phenoxy-pyridyl)-methyl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-hydroxy-3-oxo-1-propenyl)-cyclopropane-carboxylate and 0.8 ml of allyl alcohol were reacted and the oil residue was chromatographed over silica gel. Elution with an 85-15 n-hexane-ethyl acetate mixture yielded 1.55 g of (R, S) cyano-2-(6-phenoxy-pyridyl)-methyl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-allyloxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+53°±3° (c=0.3% in chloroform).

Workup

  1. customwere reacted
  2. customthe oil residue was chromatographed over silica gel
  3. washElution with an 85-15 n-hexane-ethyl acetate mixture

Sources & evidence

ORD record
ord-44e8d38594a248e3aba0cad8269caec0
Source dataset
uspto-grants-1989_05
Patent number
US04833163

Reaction notes

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