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

HRID 51258

반응식

HRID 51258 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]>O1CCCC1.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

6

반응물 3

HCID 7043VeratroleHCID 133894-PyridinecarboxaldehydeHCID 178418339Butyllithium

생성물 1

HCID 314742(2,3-Dimethoxyphenyl)(4-pyridinyl)methanol

시약·촉매·용매 2

HCID 1140Toluene용매2회HCID 8028Tetrahydrofuran용매

실험 절차

In a 2 L flask, 72 g of veratrole was dissolved in 300 g of tetrahydrofuran and 155.3 g of butyllithium in toluene was added at temperatures from −10° C. to over 30° C. The mixture was stirred from 1-4 hours at ambient temperature. Then 40 g of 4-pyridinecarboxaldehyde (9) in 180 mL of toluene was added around ambient temperature. The reaction mixture was stirred from 30 minutes to 5 hours. The solution was then cooled to around 5° C. and quenched with 200 mL of water. The phases were separated and the organic phase was distilled to remove the tetrahydrofuran. The residue was taken up in toluene at −5° C. The 4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]pyridine (10) was collected by filtration and washed with 60 g of toluene.

후처리

  1. stirringThe reaction mixture was stirred from 30 minutes to 5 hours
  2. temperatureThe solution was then cooled to around 5° C.
  3. customquenched with 200 mL of water
  4. customThe phases were separated
  5. distillationthe organic phase was distilled
  6. customto remove the tetrahydrofuran
  7. customwas taken up in toluene at −5° C
  8. filtrationThe 4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]pyridine (10) was collected by filtration
  9. washwashed with 60 g of toluene

출처 및 근거

ORD 기록
ord-0e4920b4fa6d46fc9989904dad9cec22
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06713627B2

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