Sulfuric Acid → HCID 178448151、化合物

HRID 372924ノート

反応式

HRID 372924 の反応式
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[CH:12][C:11]([CH:14]=[O:15])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:16]([CH:19]([CH2:22]O)[CH2:20][OH:21])[CH2:17][CH3:18].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH2:16]([C@@H:19]1[CH2:20][O:21][C@@H:14]([C:11]2[CH:10]=[CH:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)=[N:13][CH:12]=2)[O:15][CH2:22]1)[CH2:17][CH3:18]

参加物

5

反応物 3

HCID 1118Sulfuric AcidHCID 70211562-propylpropane-1,3-diolHCID 198125906-(4-Fluorophenyl)nicotinaldehyde

生成物 1

HCID 178448151HCID 178448151、化合物収率 22.5%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 1.51 g of 6-(4-fluorophenyl)-3-pyridinecarboxaldehyde and 1.10 g of 2-propyl-1,3-propanediol in 50 ml of toluene was treated with 10 drops of 10 percent (v/v) sulphuric acid. The mixture was heated to boiling for 1.5 hours, whereby moist toluene was distilled off and replaced by fresh toluene. Then, the reaction mixture was neutralized with triethylamine and, after cooling, washed three times with water, dried over sodium sulphate and concentrated. Chromatographic purification of the residue on 60 g of silica gel with toluene/acetone (vol. 99:1) and two-fold recrystallization of the trans/cis mixture from hexane/ethyl acetate (vol. 1:1) gave 0.51 g of pure 5-(trans-5-propyl-1,3-dioxan-2-yl)-2-(4-fluorophenyl)pyridine; m.p. (C-SA) 106.5° C., SA -N 117.5° C., cl.p. (N-I) 163° C.

後処理

  1. temperatureThe mixture was heated
  2. distillationwhereby moist toluene was distilled off
  3. temperatureafter cooling
  4. washwashed three times with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated
  7. customChromatographic purification of the residue on 60 g of silica gel
  8. customwith toluene/acetone (vol. 99:1) and two-fold recrystallization of the trans/cis mixture from hexane/ethyl acetate (vol. 1:1)

出典と根拠

ORDレコード
ord-7871f92cb102441dba497f57a1bcb35c
出典データセット
uspto-grants-1992_11
特許番号
US05160661

反応ノート

読み込み中…