Hydrochloric Acid → 2-(8-Hydroxy-7-oxo-octyl)cyclopent-2-en-1-one

HRID 126734ノート

反応式

HRID 126734 の反応式
Cl[C:2]([CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1)=[O:3].[O:16]1CCOC[CH2:17]1.Cl>[Cl-].[Na+].O>[OH:16][CH2:17][C:2](=[O:3])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:11](=[O:15])[CH2:12][CH2:13][CH:14]=1

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 202875962-[6-(Chloroformyl)hexyl]cyclopent-2-en-1-one

生成物 1

HCID 202876282-(8-Hydroxy-7-oxo-octyl)cyclopent-2-en-1-one

試薬・触媒・溶媒 1

HCID 57417360Sodium chloride; water溶媒

反応条件

温度
80 °C

実験手順

A mixture of 6.3 g. of 2-[6-(chloroformyl)hexyl]-cyclopent-2-en-1-one (Example 75) and 16 g. of tris-trimethylsilyloxyethylene (Example 74) are stirred at 90° to 100° C. under argon for one hour. To this mixture is added 25 ml. of dioxane and 10 ml. of 0.6N hydrochloric acid. The mixture is heated at 80° C. for 30 minutes. The mixture is poured into brine and extracted with ether. The ether solution is washed with saturated sodium bicarbonate and dried over magnesium sulfate. The solvent is removed and the residue is chromatographed on a dry column of silica gel eluting with ether containing 2% acetic acid to give 1.7 g. of the title compound (Rf =0.45).

後処理

  1. additionA mixture of 6.3 g
  2. additionTo this mixture is added 25 ml
  3. extractionextracted with ether
  4. washThe ether solution is washed with saturated sodium bicarbonate
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is removed
  7. customthe residue is chromatographed on a dry column of silica gel eluting with ether containing 2% acetic acid
  8. customto give 1.7 g

出典と根拠

ORDレコード
ord-e6d99089f33c41beb69c201e5abb07da
出典データセット
uspto-grants-1981_03
特許番号
US04254036

反応ノート

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