p-Toluenesulfonic acid → Pirandamine

HRID 1731144

반응식

HRID 1731144 반응식
[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][C:5](=O)[CH3:6].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:20]1[C:28]2[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=2)[C:22]([CH2:29][CH2:30][OH:31])=[CH:21]1.B(F)(F)F.CCOCC>C1(C)C=CC=CC=1.O>[CH3:1][N:2]([CH3:8])[CH2:3][CH2:4][C:5]1([CH3:6])[C:21]2[CH2:20][C:28]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:22]=2[CH2:29][CH2:30][O:31]1

참가 물질

7

반응물 4

HCID 6101p-Toluenesulfonic acidHCID 8000Boron trifluoride etherateHCID 5469134-(Dimethylamino)butan-2-oneHCID 113556481H-Indene-3-ethanol

생성물 1

HCID 431429Pirandamine

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매2회

반응 조건

온도
80 °C

실험 절차

To a solution of 1-dimethylamino-3-butanone (1.0 g) dissolved in toluene (10 ml), p-toluenesulfonic acid (1.3 g) is added. The suspension is stirred for 10 min. Indene-3-ethanol (1.0 g) in toluene (5 ml) is added to the suspension and the resulting solution stirred for 2 hr. Boron trifluoride etherate (0.25 ml) is added together with ca. 0.5 g of hydrated alkali-aluminum silicate. The mixture is heated at 80° C for 30 min. The mixture is cooled and diluted with water. The organic layer is separated and the aqueous layer extracted with toluene. The organic layers are washed with water. The combined aqueous phase is rendered alkaline with conc.NH4OH and extracted with toluene. The latter extract is treated with charcoal and then concentrated to afford the title compound, identical to the compound of the same name described in Example 284.

후처리

  1. stirringthe resulting solution stirred for 2 hr
  2. temperatureThe mixture is cooled
  3. customThe organic layer is separated
  4. extractionthe aqueous layer extracted with toluene
  5. washThe organic layers are washed with water
  6. extractionNH4OH and extracted with toluene
  7. extractionThe latter extract
  8. additionis treated with charcoal
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0aee8ca12c14417f8d9857acf2f2de25
출처 데이터셋
uspto-grants-1976_11
특허 번호
US03995052

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