Oxygen → 2-(3-chloro-phenyl)-2H-tetrazol-5-yl-ethanol

HRID 639840노트

반응식

HRID 639840 반응식
O=[O+][O-].[Cl:4][C:5]1[CH:6]=[C:7]([N:11]2[N:15]=[N:14][C:13]([C:16]([CH3:24])=CC3C=CC=CC=3)=[N:12]2)[CH:8]=[CH:9][CH:10]=1.[O:25]=O.[BH4-].[Na+]>CO.ClCCl>[Cl:4][C:5]1[CH:6]=[C:7]([N:11]2[N:15]=[N:14][C:13]([CH:16]([OH:25])[CH3:24])=[N:12]2)[CH:8]=[CH:9][CH:10]=1

참가 물질

7

반응물 4

HCID 977OxygenHCID 24823OzoneHCID 4311764Sodium borohydrideHCID 684297432-(3-chlorophenyl)-5-[1-methyl-2-phenylvinyl]-2H-tetrazole

생성물 1

HCID 594242172-(3-chloro-phenyl)-2H-tetrazol-5-yl-ethanol수율 87%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

Ozone was bubbled through a solution of 2-(3-chlorophenyl)-5-[1-methyl-2-phenylvinyl]-2H-tetrazole (2.73 g, 9.2 mmol) in methanol (75 mL) and dichloromethane (75 mL) at −78° C. When the color lightened and the starting material had disappeared by TLC, oxygen was bubbled through the mixture for approximately 2-3 minutes. Sodium borohydride (635 mg, 16.8 mmol) was added. The reaction was allowed to warm to room temperature, stirred for 30 minutes and quenched with water (5 mL) and saturated ammonium chloride (5 mL). After removal of the solvent in vacuo, the product was partitioned between dichloromethane and water, dried over sodium sulfate, and the solvent was removed in vacuo. Flash chromatography (15-35% ethyl acetate in hexane) yielded the title compound as a yellow solid (1.795 g, 87%). 1H NMR (CDCl3) δ (ppm): 8.19 (m, 1H), 8.06 (m, 1H), 7.50 (m, 2H), 5.3 (m, 1H), 2.54 (m, 1H), 1.78 (d, 3H).

후처리

  1. customwas bubbled through the mixture for approximately 2-3 minutes
  2. customquenched with water (5 mL) and saturated ammonium chloride (5 mL)
  3. customAfter removal of the solvent in vacuo
  4. customthe product was partitioned between dichloromethane and water
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was removed in vacuo

출처 및 근거

ORD 기록
ord-781e91004c6a44bd88ed2b869fe9e7b0
출처 데이터셋
uspto-grants-2010_04
특허 번호
US07691892B2

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