Acetic Acid → 2-Decyloxy-5-(p-hydroxyphenyl)pyrimidine (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoate

HRID 1728431ノート

反応式

HRID 1728431 の反応式
[CH2:1]([O:11][C:12]1[N:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=2)=[CH:14][N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].N1(C2C=CN=CC=2)CCCC1.C1(N=C=NC2CCCCC2)CCCCC1.C(O)(=O)C.[CH2:55]([O:61][CH:62]([C:67]1[CH:75]=[CH:74][C:70]([C:71]([OH:73])=[O:72])=[CH:69][CH:68]=1)[C:63]([F:66])([F:65])[F:64])[CH2:56][CH2:57][CH2:58][CH2:59][CH3:60]>ClCCl>[CH2:55]([O:61][CH:62]([C:67]1[CH:75]=[CH:74][C:70]([C:71]([OH:73])=[O:72])=[CH:69][CH:68]=1)[C:63]([F:65])([F:66])[F:64])[CH2:56][CH2:57][CH2:58][CH2:59][CH3:60].[CH2:1]([O:11][C:12]1[N:17]=[CH:16][C:15]([C:18]2[CH:19]=[CH:20][C:21]([OH:24])=[CH:22][CH:23]=2)=[CH:14][N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

参加物

7

反応物 5

HCID 176Acetic AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 190180752-Decyloxy-5-(p-hydroxyphenyl)pyrimidineHCID 19018076(+)-4-(1-Hexyloxy-2,2,2-trifluoroethyl)benzoic acid

生成物 1

HCID 867479682-Decyloxy-5-(p-hydroxyphenyl)pyrimidine (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoate収率 82%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

In 20 ml of dry dichloromethane were dissolved 3.04 g of (10 millimoles) of optically active (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoic acid, 3.28 g (10 millimoles) of 2-decyloxy-5-(p-hydroxyphenyl)pyrimidine and 0.2 g of 4-pyrrolidinopyridine. Then, 2.5 g (12 millimoles) of dicyclohexylcarbodiimide was added and the resulting mixture was stirred at room temperature for 6 hours. After the reaction, 5% aqueous solution of acetic acid was added and the whole was extracted with dichloromethane. The organic layer was washed successively with water and 7% aqueous solution of sodium hydrogen carbonate and dried on anhydrous magnesium sulfate, and then the solvent was distilled off and the residue was purified by silica gel column chromatography. Thus, 5.05 g (yield 82%) of optically active 2-decyloxy-5-(p-hydroxyphenyl)pyrimidine (+)-4-(1-hexyloxy-2,2,2-trifluoroethyl)benzoate was obtained.

後処理

  1. additionwas added
  2. extractionthe whole was extracted with dichloromethane
  3. washThe organic layer was washed successively with water and 7% aqueous solution of sodium hydrogen carbonate
  4. dry with materialdried on anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off
  6. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-d35929fba4e64311a6c72d1411ddc73f
出典データセット
uspto-grants-1994_07
特許番号
US05326871

反応ノート

読み込み中…