Water → 7-{7-(3-Oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[4,4]-non-6-yl}heptanoic acid

HRID 259203ノート

反応式

HRID 259203 の反応式
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH:9]1[CH:17]([CH:18]=[CH:19][C:20](=[O:26])[CH2:21][O:22][CH2:23][CH2:24][CH3:25])[CH2:16][CH2:15][C:10]21[O:14][CH2:13][CH2:12][O:11]2.S(=O)(=O)(O)[OH:28].C(OCC)C.O>CN(C)C=O.[O-2].[O-2].[O-2].[Cr+6]>[O:26]=[C:20]([CH2:21][O:22][CH2:23][CH2:24][CH3:25])[CH:19]=[CH:18][CH:17]1[CH2:16][CH2:15][C:10]2([O:14][CH2:13][CH2:12][O:11]2)[CH:9]1[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][C:2]([OH:28])=[O:1]

参加物

7

反応物 4

HCID 962WaterHCID 1118Sulfuric AcidHCID 3283Diethyl EtherHCID 572413446-(7-Hydroxyhepty)-7-(3-oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[4,4]nonane

生成物 1

HCID 573107087-{7-(3-Oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[4,4]-non-6-yl}heptanoic acid

試薬・触媒・溶媒 2

HCID 10219390chromium (VI) trioxide触媒HCID 6228Dimethylformamide溶媒2 回

実験手順

Chromium trioxide (9.8 g.) (dried over phosphorus pentoxide) was added portionwise with stirring to a solution of 6-(7-hydroxyhepty)-7-(3-oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[4,4]nonane (8.6 g.) in dry dimethylformamide (130 ml.) at a temperature lower than 0° C. Concentrated sulphuric acid (3.5 ml.) in dimethylformamide (130 ml.) was added and the mixture stirred at below 10° C. for 1 hour. Diethyl ether was added followed by a minimum quantity of water to produce two readily separable layers. The ether layer was separated and stirred with aqueous 2 N sodium carbonate solution. The aqueous layer was separated, washed with diethyl ether and then covered with a layer of diethyl ether and acidified to pH 5 by the addition of 20% aqueous sodium dihydrogen phosphate solution. The ethereal layer was separated and the aqueous layer again extracted with diethyl ether. The combined ethereal layers were dried over sodium sulphate and evaporated to give 7-{7-(3-oxo-4-propoxybut-1-enyl)-1,4-dioxaspiro[ 4,4]-non-6-yl}heptanoic acid (2.1 g.),

後処理

  1. customto produce two readily separable layers
  2. customThe ether layer was separated
  3. stirringstirred with aqueous 2 N sodium carbonate solution
  4. customThe aqueous layer was separated
  5. washwashed with diethyl ether
  6. additionacidified to pH 5 by the addition of 20% aqueous sodium dihydrogen phosphate solution
  7. customThe ethereal layer was separated
  8. extractionthe aqueous layer again extracted with diethyl ether
  9. dry with materialThe combined ethereal layers were dried over sodium sulphate
  10. customevaporated

出典と根拠

ORDレコード
ord-cea396c9e8b142c197d1ec46493c1698
出典データセット
uspto-grants-1977_07
特許番号
US04036872

反応ノート

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