DL-alpha-Tocopherol → 2,5,7,8-Tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-yl 5-(3,4-dibromobutyl)pyridine-2-carboxylate

HRID 325933

反応式

HRID 325933 の反応式
[Br:1][CH:2]([CH2:14][Br:15])[CH2:3][CH2:4][C:5]1[CH:6]=[CH:7][C:8]([C:11]([OH:13])=[O:12])=[N:9][CH:10]=1.[CH3:16][C:17]1[C:26]([CH3:27])=[C:25]2[C:20]([CH2:21][CH2:22][C:23]([CH2:29][CH2:30][CH2:31][CH:32]([CH2:34][CH2:35][CH2:36][CH:37]([CH2:39][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH3:38])[CH3:33])([CH3:28])[O:24]2)=[C:19]([CH3:45])[C:18]=1O.C(N(CC)CC)C.P(Cl)(Cl)(Cl)=O>C(Cl)Cl>[CH3:27][C:26]1[C:17]([CH3:16])=[C:18]([O:12][C:11]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][CH2:3][CH:2]([Br:1])[CH2:14][Br:15])=[CH:10][N:9]=2)=[O:13])[C:19]([CH3:45])=[C:20]2[CH2:21][CH2:22][C:23]([CH2:29][CH2:30][CH2:31][CH:32]([CH2:34][CH2:35][CH2:36][CH:37]([CH2:39][CH2:40][CH2:41][CH:42]([CH3:44])[CH3:43])[CH3:38])[CH3:33])([CH3:28])[O:24][C:25]=12

参加物

6

反応物 4

HCID 2116DL-alpha-TocopherolHCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 2167205-(3,4-Dibromobutyl)pyridine-2-carboxylic acid

生成物 1

HCID 30698682,5,7,8-Tetramethyl-2-(4,8,12-trimethyltridecyl)-3,4-dihydro-2H-1-benzopyran-6-yl 5-(3,4-dibromobutyl)pyridine-2-carboxylate収率 81%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

2.42 g of 5-(3,4-dibromobutyl)picolinic acid, 2.15 g of dl-α-tocopherol and 4.0 ml of triethylamine were dissolved in 15 ml of methylene chloride, and with stirring under ice cooling, a solution of 1.0 ml of phosphorus oxychloride in 5 ml of methylene chloride was added dropwise. The reaction was performed at this temperature for 3 hours. The reaction mixture was washed with 2 N hydrochloric acid, and then with water, and dried. Then, methylene chloride was distilled off. The residue was chromatographed on a column of silica gel using benzene/ethyl acetate (4:1) as an eluent to give 3.03 g of dl-α-tocopheryl 5-(3,4-dibromobutyl)picolinate as a slightly yellow oil.

後処理

  1. washThe reaction mixture was washed with 2 N hydrochloric acid
  2. dry with materialwith water, and dried
  3. distillationThen, methylene chloride was distilled off
  4. customThe residue was chromatographed on a column of silica gel

出典と根拠

ORDレコード
ord-0801488a9c9c43d29905ce2f45f8ec31
出典データセット
uspto-grants-1984_04
特許番号
US04443459

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