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

HRID 1762641

Reaktionsgleichung

Reaktionsgleichung von HRID 1762641
[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.C1(O)CCC1>>[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].[CH3:17][C:2]1([CH3:1])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH:10]2[CH2:11][CH2:13][CH2:12]2)=[O:8])[CH:3]1[C:14]([O-:16])=[O:15]

Komponenten

5

Edukt 3

HCID 76218CyclobutanolHCID 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

Produkt 2

HCID 539155962,2-Dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acidHCID 736755712,2-Dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate

Versuchsvorschrift

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 1 ml of cyclobutanol were reacted and the oil residue was chromatographed over silica gel. Elution with an 8-1 cyclohexane-ethyl acetate mixture yielded 1.6 g of (R, S) cyano-2-(6-phenoxy-pyridyl)-methyl (1R, cis, ΔZ) 2,2-dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylate with a specific rotation of [α]D20 =+44.5°±2° (c=0.5% in benzene).

Aufarbeitung

  1. customwere reacted
  2. customthe oil residue was chromatographed over silica gel
  3. washElution with an 8-1 cyclohexane-ethyl acetate mixture

Quellen und Nachweise

ORD-Eintrag
ord-7a8c1cbc0d3841369c620924bb164f55
Quelldatensatz
uspto-grants-1989_05
Patentnummer
US04833163

Verknüpfte Notizen

Wird geladen…