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Sodium Bicarbonate → (S)-ethyl 2-tert-butoxy-2-(1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate

HRID 926174
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HRID 926174 반응식
[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[C:13]=1[O:24]S(C(F)(F)F)(=O)=O)[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(O)=O.[Na+]>C1COCC1>[C:1]([O:5][C@@H:6]([C:12]1[C:21]([CH3:22])=[CH:20][C:19]2[C:14](=[CH:15][CH:16]=[C:17]([CH3:23])[CH:18]=2)[C:13]=1[OH:24])[C:7]([O:9][CH2:10][CH3:11])=[O:8])([CH3:4])([CH3:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 516892Sodium BicarbonateHCID 2724141Tetrabutylammonium FluorideHCID 89681723(S)-ethyl 2-tert-butoxy-2-(3,6-dimethyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

생성물 1

HCID 89681728(S)-ethyl 2-tert-butoxy-2-(1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (S)-ethyl 2-tert-butoxy-2-(3,6-dimethyl-1-(trifluoromethyl-sulfonyloxy) naphthalen-2-yl)acetate (1.8 g, 3.9 mmol) in THF (18.2 mL) pre-cooled to −10° C. was treated dropwise with tetrabutylammonium fluoride (1M in THF, 7.8 mL, 7.8 mmol). After 1 hour, saturated NaHCO3 was added and the mixture stirred for 20 minutes. Following extraction of the aqueous layer with EtOAc, the combined organics were washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. Purification via Yamazen silica gel column chromatography afforded (S)-ethyl 2-tert-butoxy-2-(1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate. LCMS-ESI− (m/z): [M−H]− calcd for C20H25O4: 329.4. found: 329.1.

후처리

  1. extractionextraction of the aqueous layer 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 silica gel column chromatography

출처 및 근거

ORD 기록
ord-0d8f41e7d5454683b9161bdf2d5d3520
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09284323B2

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