Tetrabutylammonium Fluoride → (S)-ethyl 2-(6-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

HRID 926187노트

반응식

HRID 926187 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([O:12]S(C(F)(F)F)(=O)=O)=[C:7]([C@H:20]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:6]([CH3:31])=[CH:5]2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8]([OH:12])=[C:7]([C@H:20]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:6]([CH3:31])=[CH:5]2

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 89681724(S)-ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate

생성물 1

HCID 89681727(S)-ethyl 2-(6-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of (S)-ethyl 2-(6-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate (260 mg, 0.5 mmol) in anhydrous THF (4 mL) at 0° C. was added a 1N tetrabutylammonium fluoride in THF (0.6 mL, 0.6 mmol) and stirred for 1 hour. The reaction was quenched by the addition saturated NaHCO3 solution and extracted using EtOAc. The organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 5 to 30% ethyl acetate/hexanes) to give the desired compound. LCMS-ESI− (m/z): [M−H]− calcd for C19H22BrO4: 394.29. Found: 394.0.

후처리

  1. customThe reaction was quenched by the addition saturated NaHCO3 solution
  2. extractionextracted
  3. dry with materialThe organic layer was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. custompurified by flash column chromatography (silica gel, 5 to 30% ethyl acetate/hexanes)

출처 및 근거

ORD 기록
ord-84bb6cc8a4e943e99118419e61cbdde8
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09284323B2

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