Sulfuric Acid → HCID 178448151, 화합물

HRID 372924노트

반응식

HRID 372924 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 178448151HCID 178448151, 화합물수율 22.5%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-7871f92cb102441dba497f57a1bcb35c
출처 데이터셋
uspto-grants-1992_11
특허 번호
US05160661

반응 노트

불러오는 중…