Sodium Bicarbonate → 3-(10-Hydroxydecyl)-4-methyl-2-cyclohexene-1-one

HRID 1375124ノート

反応式

HRID 1375124 の反応式
C1CO[C:3]2([CH2:8][CH2:7][CH:6]([CH3:9])[C:5]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][OH:29])(S(C3C=CC=CC=3)(=O)=O)[CH2:4]2)[O:2]1.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl.CC(C)=O>[OH:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][C:5]1[CH:6]([CH3:9])[CH2:7][CH2:8][C:3](=[O:2])[CH:4]=1

参加物

5

反応物 2

HCID 516892Sodium BicarbonateHCID 219991391,1-(Ethylenedioxy)-3-(10-hydroxydecyl)-4-methyl-3-(phenylsulfonyl)-cyclohexane

生成物 1

HCID 106354973-(10-Hydroxydecyl)-4-methyl-2-cyclohexene-1-one収率 75%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6212Chloroform溶媒

実験手順

Paratoluenesulfonic acid (20 ml) was added to a solution of 235 mg of 1,1-(ethylenedioxy)-3-(10-hydroxydecyl)-4-methyl-3-(phenylsulfonyl)-cyclohexane in 20 ml of chloroform and 4 ml of acetone. The resulting mixture was reacted at 50° C. for 24 hours. To the reaction mixture were added 10 ml of a saturated aqueous solution of sodium bicarbonate, followed by extraction with dichloromethane. The organic layer was washed with saturated saline and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by chromatography on a silica gel column while using hexane-ethyl acetate, whereby 3-(10-hydroxydecyl)-4-methyl-2-cyclohexene-1-one was obtained in the form of a colorless oil. Yield: 75%, CCM: (hexane-AcOEt: 6-4) Rf=0.2

後処理

  1. customThe resulting mixture was reacted at 50° C. for 24 hours
  2. extractionfollowed by extraction with dichloromethane
  3. washThe organic layer was washed with saturated saline
  4. dry with materialdried over magnesium sulfate
  5. distillationThe solvent was distilled off under reduced pressure
  6. customThe residue was purified by chromatography on a silica gel column

出典と根拠

ORDレコード
ord-53199389c18941439e07949facfb6c19
出典データセット
uspto-grants-2007_01
特許番号
US07166642B1

反応ノート

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