3-Pyridinecarboxaldehyde → 2-[(3-Pyridyl)hydroxymethyl]-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene

HRID 35191노트

반응식

HRID 35191 반응식
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:12]3([CH3:17])[O:16][CH2:15][CH2:14][O:13]3)[CH:8]=2)[CH:3]=1.C([Li])(C)(C)C.[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]=[O:30])[CH:24]=1>O1CCCC1>[N:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH:29]([OH:30])[C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[CH:5][CH:6]=[C:7]([C:12]4([CH3:17])[O:16][CH2:15][CH2:14][O:13]4)[CH:8]=3)[CH:3]=2)[CH:24]=1

참가 물질

5

반응물 3

HCID 103713-PyridinecarboxaldehydeHCID 136879082-(6-Bromonaphthalen-2-yl)-2-methyl-1,3-dioxolaneHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 156122412-[(3-Pyridyl)hydroxymethyl]-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene수율 63%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 4.5 g of 2-bromo-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene in 30 ml of tetrahydrofuran was cooled to -78° C. under nitrogen, and 14.0 ml of 2.2M t-butyl lithium added dropwise. A solution of 1.64 g of 3-pyridinecarboxaldehyde in 15 ml of tetrahydrofuran was added over a period of 10 minutes, and the temperature was allowed to rise to -20° C. during the next 30 minutes. The reaction was quenched with 30 ml of water and the mixture extracted with methylene chloride. The organic layer was dried over sodium sulfate and solvent removed under reduced pressure to give a solid that was recrystallized from methylene chloride/diethyl ether to give 3.1 g of 2-[(3-pyridyl)hydroxymethyl]-6-(2-methyl-1,3-dioxolan-2-yl)naphthalene, m.p. 154°-156° C.

후처리

  1. customto rise to -20° C. during the next 30 minutes
  2. customThe reaction was quenched with 30 ml of water
  3. extractionthe mixture extracted with methylene chloride
  4. dry with materialThe organic layer was dried over sodium sulfate and solvent
  5. customremoved under reduced pressure
  6. customto give a solid
  7. customthat was recrystallized from methylene chloride/diethyl ether

출처 및 근거

ORD 기록
ord-91ab7496c7d048febe8a88218f6c8816
출처 데이터셋
uspto-grants-1988_08
특허 번호
US04766127

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