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

HRID 514060ノート

反応式

HRID 514060 の反応式
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]

参加物

5

反応物 3

HCID 24247Perchloric AcidHCID 516892Sodium Bicarbonate2 回HCID 86691546(S)-ethyl 2-(1-(4-chlorophenyl)-3-methyl-6-(trifluoromethylsulfonyloxy) naphthalen-2-yl)-2-hydroxyacetate

生成物 1

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

試薬・触媒・溶媒 1

HCID 10908tert-Butyl acetate溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-830b9125f629475c84cb7d29bb5b6adf
出典データセット
uspto-grants-2015_08
特許番号
US09102614B2

反応ノート

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