Veratrole → (2,3-Dimethoxyphenyl)(4-pyridinyl)methanol

HRID 51259

반응식

HRID 51259 반응식
C([Li])CCC.[N:6]1[CH:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][CH:7]=1.[C:14]1([O:22][CH3:23])[C:15](=[CH:18][CH:19]=[CH:20][CH:21]=1)[O:16][CH3:17]>C1(C)C=CC=CC=1>[OH:13][CH:12]([C:9]1[CH:10]=[CH:11][N:6]=[CH:7][CH:8]=1)[C:21]1[CH:20]=[CH:19][CH:18]=[C:15]([O:16][CH3:17])[C:14]=1[O:22][CH3:23]

참가 물질

5

반응물 3

HCID 7043VeratroleHCID 133894-PyridinecarboxaldehydeHCID 178418339Butyllithium

생성물 1

HCID 314742(2,3-Dimethoxyphenyl)(4-pyridinyl)methanol수율 81.8%

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
5 °C

실험 절차

In a 2 L flask, 48 g of veratrole was dissolved in 200 g of toluene and 138 g of butyl lithium solution (15% in hexane) were added at temperatures from 4° C. to 6° C. The mixture was stirred for one hour at about 5° C. and 3 hours at ambient temperature. Then 26.7 g of 4-pyridinecarboxaldehyde (9) in 120 g of toluene was added at around ambient temperature. The reaction mixture was stirred for about 4.5 hours. The mixture was then cooled to around 5° C. and quenched with 133 mL of water. The mixture was then heated to around 80° C. The organic layer was separated, washed with 67 mL of water and separated. The residual water was removed by azeotropic distillation. The solution was then cooled to −15° C. to −5° C. The product was collected by filtration and washed with 27 g of cold toluene. The yield was 50 g of 4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]pyridine (10) (81% yield).

후처리

  1. stirringThe reaction mixture was stirred for about 4.5 hours
  2. temperatureThe mixture was then cooled to around 5° C.
  3. customquenched with 133 mL of water
  4. temperatureThe mixture was then heated to around 80° C
  5. customThe organic layer was separated
  6. washwashed with 67 mL of water
  7. customseparated
  8. customThe residual water was removed by azeotropic distillation
  9. temperatureThe solution was then cooled to −15° C. to −5° C
  10. filtrationThe product was collected by filtration
  11. washwashed with 27 g of cold toluene

출처 및 근거

ORD 기록
ord-71428b8a2c6f477cadf138c1c314667f
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713627B2

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