Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]- → (E)-3-[4-(2-Pyrimidinyl)phenyl]-2-propenal

HRID 50564

반응식

HRID 50564 반응식
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[CH:14]=[CH:13][C:10]([CH:11]=O)=[CH:9][CH:8]=1.[Br-].[O:16]1CCO[CH:17]1[CH2:21][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.COCCOCCN(CCOCCOC)CCOCCOC>ClCCl.C([O-])([O-])=O.[K+].[K+]>[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[C:7]1[CH:14]=[CH:13][C:10](/[CH:11]=[CH:21]/[CH:17]=[O:16])=[CH:9][CH:8]=1

참가 물질

6

반응물 3

HCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 2724194(1,3-Dioxolan-2-ylmethyl)triphenylphosphonium bromideHCID 127037224-(Pyrimidin-2-yl)benzaldehyde

생성물 1

HCID 22630870(E)-3-[4-(2-Pyrimidinyl)phenyl]-2-propenal수율 57.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 11430Potassium Carbonate용매

실험 절차

A mixture of 4-(2-pyrimidinyl)-benzaldehyde (1.83 g, 9.94 mmol, prepared as described in WO 9828264), (1,3-dioxolan-2-ylmethyl)triphenylphosphonium bromide (6.45 g, 15.02 mmol), and TDA-1 (3.20 mL, 10.00 mmol) in dichloromethane (50 mL) and sat. aq. K2CO3 (50 mL) was heated to reflux for 20 h. The layers were separated and the aqueous layer was extracted with dichloromethane (2×25 mL). The combined organic layers were washed with water (50 mL) and brine (50 mL), dried (MgSO4), and concentrated. THF (25 mL) and 10% HCl (25 mL) were added and the mixture was stirred for 1 h at rt. The mixture was cooled to 0° C., the precipitated solids were removed by filtration, washed with water and air-dried. Recrystallization from 2-propanol provided 1.20 g (57%) of the title compound as a light yellow solid. MS 211 (M+H)+.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 20 h
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (2×25 mL)
  5. washThe combined organic layers were washed with water (50 mL) and brine (50 mL)
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. additionTHF (25 mL) and 10% HCl (25 mL) were added
  9. temperatureThe mixture was cooled to 0° C.
  10. customthe precipitated solids were removed by filtration
  11. washwashed with water
  12. customair-dried
  13. customRecrystallization from 2-propanol

출처 및 근거

ORD 기록
ord-4da97e34da684bd08056b982ffd70aea
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713455B2

연결된 노트

불러오는 중…