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

HRID 51257

反応式

HRID 51257 の反応式
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]

参加物

5

反応物 3

HCID 7043VeratroleHCID 133894-PyridinecarboxaldehydeHCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒3 回

実験手順

In a 2 L flask, 72 g of veratrole was dissolved in 300 g of toluene and 155.3 g of butyl lithium in toluene were 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 at 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 solution was then heated to 40-85° C. and subsequently cooled to −5° C. The product was collected by filtration and washed with 60 g of water and 60 g of toluene. The yield was about 80 g of 4-[1-hydroxy-1-(2,3-dimethoxyphenyl)methyl]pyridine (10).

後処理

  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. temperatureThe solution was then heated to 40-85° C.
  5. temperaturesubsequently cooled to −5° C
  6. filtrationThe product was collected by filtration
  7. washwashed with 60 g of water and 60 g of toluene

出典と根拠

ORDレコード
ord-6541dad16eff493ea0d96640dc21889c
出典データセット
uspto-grants-2004_03
特許番号
US06713627B2

関連ノート

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