Benzene → Alpha-tocopherol 5-n-butyl-2-pyridinecarboxylate

HRID 325932

反応式

HRID 325932 の反応式
C1C=CC=CC=1.[CH2:7]([C:11]1[CH:12]=[CH:13][C:14]([C:17]([OH:19])=[O:18])=[N:15][CH:16]=1)[CH2:8][CH2:9][CH3:10].S(Cl)(Cl)=O.[CH3:24][C:25]1[C:34]([CH3:35])=[C:33]2[C:28]([CH2:29][CH2:30][C:31]([CH2:37][CH2:38][CH2:39][CH:40]([CH2:42][CH2:43][CH2:44][CH:45]([CH2:47][CH2:48][CH2:49][CH:50]([CH3:52])[CH3:51])[CH3:46])[CH3:41])([CH3:36])[O:32]2)=[C:27]([CH3:53])[C:26]=1O>N1C=CC=CC=1>[CH3:10][CH2:9][CH2:8][CH2:7][C:11]1[CH:12]=[CH:13][C:14]([C:17]([O:19][C:26]2[C:27]([CH3:53])=[C:28]3[CH2:29][CH2:30][C:31]([CH2:37][CH2:38][CH2:39][CH:40]([CH2:42][CH2:43][CH2:44][CH:45]([CH2:47][CH2:48][CH2:49][CH:50]([CH3:52])[CH3:51])[CH3:46])[CH3:41])([CH3:36])[O:32][C:33]3=[C:34]([CH3:35])[C:25]=2[CH3:24])=[O:18])=[N:15][CH:16]=1

参加物

6

反応物 4

HCID 241Benzene3 回HCID 2116DL-alpha-TocopherolHCID 3442Fusaric AcidHCID 24386Thionyl Chloride2 回

生成物 1

HCID 134999Alpha-tocopherol 5-n-butyl-2-pyridinecarboxylate収率 46.6%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

反応条件

温度
0 °C

実験手順

Ten milliliters of benzene was added to 4.51 g of 5-butylpicolinic acid, and 9 g of thionyl chloride was further added. The mixture was heated under reflux for 22 minutes. The excess of thionyl chloride and benzene were disiled off under reduced pressure, and 10 ml of benzene was added to the residue. The mixture was cooled to 0° C. and stirred. To the solution was added dropwise a solution of 5 g of dl-α-tocopherol in 4.25 ml of pyridine to perform the reaction for 1 hour and 40 minutes. The insoluble matter was removed by filtration from the reaction mixture, and the residue was washed with water, 1 N hydrochloric acid, water, a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride in this order. Benzene was distilled off, and the residue was chromatographed on a silica gel column using benzene/ethyl acetate (4:1) as an eluent to give 3.2 g of dl-α-tocopheryl 5-butylpicolinate.

後処理

  1. additionwas further added
  2. temperatureThe mixture was heated
  3. temperatureunder reflux for 22 minutes
  4. additionwas added to the residue
  5. customthe reaction for 1 hour
  6. custom40 minutes
  7. customThe insoluble matter was removed by filtration from the reaction mixture
  8. washthe residue was washed with water, 1 N hydrochloric acid, water
  9. distillationBenzene was distilled off
  10. customthe residue was chromatographed on a silica gel column

出典と根拠

ORDレコード
ord-e84cd651b4b24211a96cb2372b7b515a
出典データセット
uspto-grants-1984_04
特許番号
US04443459

関連ノート

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