Hydrochloric Acid → Methyl 8-methylsulfonyl-12-acetoxyheptadecanoate

HRID 328766ノート

反応式

HRID 328766 の反応式
COC([C:5]([S:29]([CH3:32])(=[O:31])=[O:30])([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=O.[Cl-].[Na+].CS(C)=O.Cl>O>[CH3:32][S:29]([CH:5]([CH2:16][CH2:17][CH2:18][CH:19]([O:25][C:26](=[O:28])[CH3:27])[CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])(=[O:30])=[O:31]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 5234Sodium ChlorideHCID 21317603Methyl 8-methoxycarbonyl-8-methylsulfonyl-12-acetoxyheptadecanoate

生成物 1

HCID 21317665Methyl 8-methylsulfonyl-12-acetoxyheptadecanoate収率 95.7%

試薬・触媒・溶媒 1

HCID 962Water溶媒2 回

反応条件

温度
185 °C

実験手順

A mixture of methyl 8-methoxycarbonyl-8-methylsulfonyl-12-acetoxyheptadecanoate (36.7 g., 0.077 mole), sodium chloride (4.68 g., 0.08 mole), water (1 ml.) and dimethylsulfoxide (60 ml.) is heated in a bath maintained at 185° C. under nitrogen for 5 hours. The resulting reaction mixture is concentrated in vacuo at 100° C. providing an oily residue which is diluted with water. The aqueous mixture is acidified to Congo Red with 6N hydrochloric acid and extracted with ether. The organic extract is washed with water, dried over magnesium sulfate, filtered and evaporated in vacuo leaving the title compound as a viscous oil (31 g., 95%), pmr (CDCl3) δ2.0 (s, 3H), 2.82 (s, 3H), 3.63 (s, 3H) and 4.9 (b, H).

後処理

  1. temperatureis heated in a bath
  2. customThe resulting reaction mixture
  3. concentrationis concentrated in vacuo at 100° C.
  4. customproviding an oily residue which
  5. extractionextracted with ether
  6. extractionThe organic extract
  7. washis washed with water
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. customevaporated in vacuo

出典と根拠

ORDレコード
ord-924867ce4a124a23ae496e98ee8b0c04
出典データセット
uspto-grants-1977_04
特許番号
US04018802

反応ノート

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