Sodium potassium tartrate tetrahydrate → [6-Bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-methanol

HRID 238634

반응식

HRID 238634 반응식
C[O:2][C:3]([C:5]1[CH:14]=[C:13]([O:15][C:16]2[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH3:26])(=[O:24])=[O:23])=[CH:18][N:17]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:27])[CH:11]=2)[CH:6]=1)=O.[H-].C([Al+]CC(C)C)C(C)C.O.O.O.O.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>O1CCCC1>[Br:27][C:10]1[CH:11]=[C:12]2[C:7](=[CH:8][CH:9]=1)[CH:6]=[C:5]([CH2:3][OH:2])[CH:14]=[C:13]2[O:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH2:25][CH3:26])(=[O:23])=[O:24])=[CH:18][N:17]=1

참가 물질

5

반응물 3

HCID 2724148Sodium potassium tartrate tetrahydrateHCID 21225700DiisobutylaluminumhydrideHCID 593266036-Bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalene-2-carboxylic acid methyl ester

생성물 1

HCID 59326541[6-Bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-methanol수율 99%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 6-bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalene-2-carboxylic acid methyl ester (280 mg, 0.63 mmol) in tetrahydrofuran (5 mL) was added a solution of diisobutylaluminum hydride (1 M in toluene, 1.3 mL, 1.3 mmol) dropwise at −78° C. under a nitrogen atmosphere. The resulting mixture was warmed to room temperature and stirred at room temperature (the total stirring time between −78° C. and room temperature was 3 hours). The reaction mixture was treated with an aqueous solution of potassium sodium tartrate tetrahydrate at 0° C., warmed to room temperature, and stirred at room temperature for 30 min. The resulting mixture was extracted with ethyl acetate (20 mL×3). The combined organic layers were washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by silica gel chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether) to give [6-bromo-4-(5-ethanesulfonyl-pyridin-2-yloxy)-naphthalen-2-yl]-methanol (263 mg, 99%) as a colorless oil.

후처리

  1. temperaturewarmed to room temperature
  2. stirringstirred at room temperature for 30 min
  3. extractionThe resulting mixture was extracted with ethyl acetate (20 mL×3)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel chromatography (silica gel, 100-200 mesh, 30% ethyl acetate in petroleum ether)

출처 및 근거

ORD 기록
ord-d4f90def062f47af9dd00947c8559b93
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642629B2

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