tert-Butyl acetate → Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

HRID 514145노트

반응식

HRID 514145 반응식
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)=[C:4]([CH:19]([OH:24])[C:20]([O:22][CH3:23])=[O:21])[C:3]=1[CH3:25].[C:26](OC(C)=O)([CH3:29])([CH3:28])[CH3:27].C([O-])(O)=O.[Na+]>Cl(O)(=O)(=O)=O>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12]2[CH:13]=[CH:14][C:15]([Cl:18])=[CH:16][CH:17]=2)=[C:4]([CH:19]([O:24][C:26]([CH3:29])([CH3:28])[CH3:27])[C:20]([O:22][CH3:23])=[O:21])[C:3]=1[CH3:25]

참가 물질

5

반응물 3

HCID 10908tert-Butyl acetateHCID 516892Sodium BicarbonateHCID 67126228Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate

생성물 1

HCID 67126267Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-tert-butoxyacetate

시약·촉매·용매 1

HCID 24247Perchloric Acid촉매

실험 절차

Methyl 2-(4-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-hydroxyacetate (298 mg, 0.71 mmol) was dissolved in t-BuOAc (18.0 mL, 134 mmol) and 7 drops of perchloric acid were added. The reaction was monitored by HPLC and TLC for progress. After 4.5 hours, the mixture was added to icy saturated NaHCO3 and stirred for 10-15 minutes. This mixture was extracted with EtOAc, extracts dried with sodium sulfate and concentrated in vacuo. Purification on silica gel using EtOAc in hexanes gave desired product as well as some starting material. 1H-NMR: (400 MHz, CDCl3): δ 8.39 (d, J=8.8 Hz, 1H); 7.57-7.48 (m, 3H); 7.45-7.42 (m, 1H); 7.35-7.31 (m, 1H); 7.28-7.18 (m, 2H); 5.20 (s, 1H); 3.70 (s, 3H); 2.72 (s, 3H); 0.99 (s, 9H).

후처리

  1. extractionThis mixture was extracted with EtOAc
  2. dry with materialextracts dried with sodium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification on silica gel

출처 및 근거

ORD 기록
ord-2c7e6887bdbd4d6199dbc0904000809d
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102614B2

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