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

HRID 514145ノート

反応式

HRID 514145 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 24247Perchloric Acid触媒

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-2c7e6887bdbd4d6199dbc0904000809d
出典データセット
uspto-grants-2015_08
特許番号
US09102614B2

反応ノート

読み込み中…