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

HRID 1762641

반응식

HRID 1762641 반응식
[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]

참가 물질

5

반응물 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

생성물 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

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-7a8c1cbc0d3841369c620924bb164f55
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04833163

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