Perchloric Acid → (S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate

HRID 514060노트

반응식

HRID 514060 반응식
Cl(O)(=O)(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[C:22]3[C:17](=[CH:18][C:19]([O:23][S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])=[CH:20][CH:21]=3)[CH:16]=[C:15]([CH3:31])[C:14]=2[C@H:32]([OH:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[CH:9][CH:8]=1.C([O-])(O)=O.[Na+]>C(OC(C)(C)C)(=O)C>[C:10]([O:38][C@@H:32]([C:14]1[C:15]([CH3:31])=[CH:16][C:17]2[C:22](=[CH:21][CH:20]=[C:19]([O:23][S:24]([C:27]([F:30])([F:29])[F:28])(=[O:26])=[O:25])[CH:18]=2)[C:13]=1[C:10]1[CH:9]=[CH:8][C:7]([Cl:6])=[CH:12][CH:11]=1)[C:33]([O:35][CH2:36][CH3:37])=[O:34])([CH3:13])([CH3:11])[CH3:9]

참가 물질

5

반응물 3

HCID 24247Perchloric AcidHCID 516892Sodium Bicarbonate2회HCID 86691546(S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate

생성물 1

HCID 86691548(S)-ethyl 2-tert-butoxy-2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy)naphthalen-2-yl)acetate수율 116.3%

시약·촉매·용매 1

HCID 10908tert-Butyl acetate용매

실험 절차

Perchloric acid (70%, 0.28 mL, 3.2 mmol) was added to a solution of (S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate (0.82 g, 1.6 mmol) in tert-butyl acetate (5 mL) at room temperature. After 3 h, solid NaHCO3 was added and the slurry stirred vigorously for 30 min. Saturated NaHCO3 was added slowly until the mixture was pH ˜8. Following extraction of the organic layer with EtOAc, the combined organics were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The resulting residue was purified by Yamazen column chromatography (0-35% EtOAc/Hex) to produce 0.52 g (57%) of the title compound as an amorphous solid. 1H-NMR: 400 MHz, (CDCl3) δ: 7.69 (s, 1H); 7.66 (d, J=2.4 Hz, 1H); 7.51 (m, 2H); 7.44 (m, 1H); 7.34 (d, J=9.4 Hz, 1H); 7.27 (m, 1H); 7.15 (dd, J=9.4, 2.4 Hz, 1H); 5.12 (s, 1H); 4.17 (m, 2H); 2.63 (s, 3H); 1.23 (t, J=7.2 Hz, 3H); 1.01 (s, 9H).

후처리

  1. extractionextraction of the organic layer with EtOAc
  2. washthe combined organics were washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by Yamazen column chromatography (0-35% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-830b9125f629475c84cb7d29bb5b6adf
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102614B2

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