Hydrochloric Acid → HCID 178458878、化合物

HRID 1084666ノート

反応式

HRID 1084666 の反応式
[C:1]([C:5]1[C:6](=[O:31])[CH2:7][CH:8]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:19][CH:18]=2)[CH:9](C(OCC)=O)[C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3].[OH-].[Na+].Cl>C(O)C.O>[C:1]([C:5]1[C:6](=[O:31])[CH2:7][CH:8]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[CH:19][CH:18]=2)[CH2:9][C:10]=1[OH:11])(=[O:4])[CH2:2][CH3:3]

参加物

6

反応物 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 200622872-Propionyl-3-hydroxy-5-(4-benzyloxyphenyl)-4-(carboethoxy)cyclohex-2-en-1-one

生成物 1

HCID 178458878HCID 178458878、化合物

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
70 °C

実験手順

A mixture of 54 g (0.13 mol) of 2-propionyl-3-hydroxy-5-(4-benzyloxyphenyl)-4-(carboethoxy)cyclohex-2-en-1-one 30 g (0.37 mol)of 50 percent sodium hydroxide in 450 mL of 95 percent ethanol and 100 mL of water was stirred mechanically and heated at about 70° C. for 16 hours. The resulting clear yellow solution was cooled to about 60° C. and treated with 50 mL of concentrated HCl (some material was lost as the ensuing decarboxylation reaction erupted from the reaction vessel). The product precipitated from the solution and was isolated by filtration. Recrystallization from absolute ethanol gave the above named product as a beige crystalline solid in a yield of 24 g (54 percent of theoretical). The product melted at 114°-115° C.: 1H NMR (CDCl3) δ1.17 (t, 3H, --CH3), 2.60-3.48 (m, 7H, ring protons and --CH2CH3), 5.05 (s, 2H, ArCH2O--), 6.83-7.55 (m, 9H, ArH's), 18.1 (s, 1H, enol, H).

後処理

  1. temperatureThe resulting clear yellow solution was cooled to about 60° C.
  2. customwas lost as the ensuing decarboxylation reaction
  3. customThe product precipitated from the solution
  4. customwas isolated by filtration
  5. customRecrystallization from absolute ethanol
  6. customgave the

出典と根拠

ORDレコード
ord-414671d6be0e4253980c0a9fcd8d3d53
出典データセット
uspto-grants-1991_04
特許番号
US05006159

反応ノート

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