Potassium Hydroxide → Dodma

HRID 1741812노트

반응식

HRID 1741812 반응식
[CH3:1][N:2]([CH3:8])[CH2:3][CH:4]([OH:7])[CH2:5][OH:6].[OH-].[K+].S(O[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])(=O)(=O)C>C1(C)C(C)=CC=CC=1>[CH2:16]([O:7][CH:4]([CH2:5][O:6][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33])[CH2:3][N:2]([CH3:8])[CH3:1])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]/[CH:24]=[CH:25]\[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

참가 물질

5

반응물 3

HCID 14797Potassium HydroxideHCID 790783-(Dimethylamino)-1,2-propanediolHCID 6016198Oleyl methane sulfonate

생성물 1

HCID 11181107Dodma수율 76%

시약·촉매·용매 1

HCID 7237O-Xylene용매2회

실험 절차

To a three-necked, 2-liter round bottom flask equipped with a Dean-Stork trap were added 3 -dimethylamino-1,2 -propanediol (6.08 g, 51.1 mmoles), xylene (1300 ml) and KOH (8.0 g). The solution was refluxed for 2 hours while removing water azeotropically via the Dean-Stork trap. Oleyl mesylate (40.0 g, 115.6 mmoles) in 100 ml xylene was added to the reaction mixture drop-wise in 30 minutes. Refluxing was continued for 3 hours and the reaction mixture concentrated to a gum. The gum was triturated with 400 ml hexane and filtered. The solid was washed with 100 ml hexane followed with 200 ml ethyl acetate. The filtrates were combined, concentrated and subjected to f lash chromatography. 2,3-dioleyloxy-1- (N, N-dimethylamino) propane was obtained as a colorless oil in 76% yield, TLC: Rf =0.37 (Silica gel: 5% EtOAc: hexane); IR: 2925, 2850, 1469, 1120, 1040 cm-1 ; HNMR (CDCl3) δ 5.35 (t, 4H) , 4.13 (q, 1H) 3.4-3.65 (m, 6H), 2.35-2.45 (m, 2H) , 2.25 (S, 6H) , 1.95-2.05 (m, 8H) , 1.5-1.65 (m, 4H) , 1.2-1.45 (m, 4H) 0.9 (t, 6H).

후처리

  1. customTo a three-necked, 2-liter round bottom flask equipped with a Dean-Stork trap
  2. temperatureThe solution was refluxed for 2 hours
  3. customwhile removing water azeotropically via the Dean-Stork trap
  4. temperatureRefluxing
  5. concentrationthe reaction mixture concentrated to a gum
  6. customThe gum was triturated with 400 ml hexane
  7. filtrationfiltered
  8. washThe solid was washed with 100 ml hexane
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-2f15ec61c7314f8d814d38f22a35de52
출처 데이터셋
uspto-grants-1994_08
특허 번호
US05334761

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