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Sodium Bicarbonate → (S)-ethyl 2-(5-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

HRID 926176
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HRID 926176 반응식
[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:31])[C:6]([C@H:20]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:7]2[O:12]S(C(F)(F)F)(=O)=O.C(O[C@@H](C1C(C)=CC2C(=CC=C(C)C=2)C=1OS(C(F)(F)F)(=O)=O)C(OCC)=O)(C)(C)C.BrC1C=CC=CC=1CC(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1.CCOC(C)=O>[Br:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[C:5]([CH3:31])[C:6]([C@H:20]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])[C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:7]2[OH:12]
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참가 물질

8

반응물 5

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 27340921-(2-Bromophenyl)propan-2-oneHCID 89681723(S)-ethyl 2-tert-butoxy-2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetateHCID 89681749(S)-ethyl 2-(5-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate

생성물 1

HCID 89681750
(S)-ethyl 2-(5-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

A solution of (S)-ethyl 2-(5-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-tert-butoxyacetate (0.90 g, 1.7 mmol; prepared in a similar fashion to (S)-ethyl 2-tert-butoxy-2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate beginning with 1-(2-bromophenyl)propan-2-one) in THF (7 mL) cooled to 0° C. was treated with tetrabutylammonium fluoride (1M in THF, 1.7 mL, 1.7 mmol) dropwise. After 1 hour, saturated NaHCO3 and EtOAc were added and the aqueous layer extracted with EtOAc. The combined organics were washed with brine, dried over anhydrous MgSO4, filtered, and concentrated in vacuo. Purification via Yamazen column chromatography (0-15% EtOAc/hex) afforded (S)-ethyl 2-(5-bromo-1-hydroxy-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate. LCMS-ESI− (m/z): [M−H]− calcd for C19H22O4Br: 395.07. found: 395.04.

후처리

  1. extractionthe aqueous layer extracted with EtOAc
  2. washThe combined organics were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via Yamazen column chromatography (0-15% EtOAc/hex)

출처 및 근거

ORD 기록
ord-7500c315cbe643faae34b7e1500e5ff0
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284323B2

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