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

HRID 1762618ノート

反応式

HRID 1762618 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e966886adaf1485e8414f340671b5989
出典データセット
uspto-grants-1989_05
特許番号
US04833163

反応ノート

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