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

HRID 1762618

반응식

HRID 1762618 반응식
[CH3:1][C:2]1([CH3:17])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH:10]2[CH2:13][CH2:12][CH2:11]2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:17][C:2]1([CH3:1])[CH:4]([CH:5]=[CH:6][C:7]([O:9][CH2:10][CH:13]2[CH2:12][CH2:11]2)=[O:8])[CH:3]1[C:14]([OH:16])=[O:15]

참가 물질

4

반응물 2

HCID 6101p-Toluenesulfonic acidHCID 539623272,2-Dimethyl-3-(3-cyclobutoxy-3-oxo-1-propenyl)-cyclopropane-carboxylic acid

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A mixture of 12.32 g of the product of Step A, 0.6 g of p-toluene sulfonic acid and 120 ml of toluene was refluxed for 45 minutes and was cooled and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with a 7-3 n-hexane-ethyl acetate mixture containing 1% o acetic acid to obtain 8.94 g of (1R, cis, ΔZ) 2,2-dimethyl-3-(3-cyclopropylmethoxy-3-oxo-1-propenyl) cyclopropane-carboxylic acid melting at 106° C.

후처리

  1. temperaturewas refluxed for 45 minutes
  2. temperaturewas cooled
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was chromatographed over silica gel
  5. washwas eluted with a 7-3 n-hexane-ethyl acetate mixture
  6. additioncontaining 1% o acetic acid

출처 및 근거

ORD 기록
ord-e966886adaf1485e8414f340671b5989
출처 데이터셋
uspto-grants-1989_05
특허 번호
US04833163

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