Sulfuric Acid → HCID 178443321, 화합물

HRID 1030026노트

반응식

HRID 1030026 반응식
[CH2:1]([O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[N:21]=[CH:20][C:19]([CH:22]=[O:23])=[CH:18][CH:17]=2)=[CH:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH2:24]([CH:34]([CH2:37]O)[CH2:35][OH:36])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].S(=O)(=O)(O)O>C1(C)C=CC=CC=1>[CH2:24]([C@@H:34]1[CH2:35][O:36][C@@H:22]([C:19]2[CH:18]=[CH:17][C:16]([C:13]3[CH:14]=[CH:15][C:10]([O:9][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:11][CH:12]=3)=[N:21][CH:20]=2)[O:23][CH2:37]1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

참가 물질

5

반응물 3

HCID 1118Sulfuric AcidHCID 115140411,3-Propanediol, 2-decyl-HCID 19821238HCID 19821238, 화합물

생성물 1

HCID 178443321HCID 178443321, 화합물수율 17%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

A solution of 2.2 g of 6-[4-(octyloxy)phenyl]-3-pyridinecarboxaldehyde (prepared in accordance with Example 2) and 1.4 g of 2-decyl-1,3-propanediol in 40 ml of toluene was treated with 5 drops of 10 percent (v/v) sulfuric acid. The mixture was heated to boiling for 1 hour, moist toluene being distilled off and being replaced by fresh toluene. The reaction mixture was then neutralized with triethylamine and, after cooling, washed three times with water, dried over sodium sulfate and concentrated. Chromatographic purification of the residue on 60 g of silica gel with hexane/ethyl acetate (vol. 9:1) and repeated recrystallization of the trans/cis mixture from ethyl acetate gave 0.56 g of pure 5-(trans-5-decyl-1,3-dioxan-2-yl)-2-[4-(octyloxy)phenyl]pyridine; m.p. (C-S) 69.7° C., transition S-SC 137.5° C., cl.p. (SC -I) 179° C.

후처리

  1. temperatureThe mixture was heated
  2. distillationmoist toluene being distilled off
  3. temperatureafter cooling
  4. washwashed three times with water
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated
  7. customChromatographic purification of the residue on 60 g of silica gel with hexane/ethyl acetate (vol. 9:1)
  8. customrecrystallization of the trans/cis mixture from ethyl acetate

출처 및 근거

ORD 기록
ord-20e92b1986304f4fa1fd49847c80af6a
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05104569

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