Water → tert-Butyl 7-ethoxynaphthalen-1-ylcarbamate

HRID 416124ノート

反応式

HRID 416124 の反応式
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:27][CH3:28].O>CN(C=O)C>[CH2:27]([O:1][C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][CH:8]=[C:9]2[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[CH:4][CH:3]=1)[CH3:28]

参加物

6

反応物 4

HCID 962WaterHCID 6340IodoethaneHCID 10796Cesium carbonateHCID 18536180tert-Butyl (7-hydroxynaphthalen-1-yl)carbamate

生成物 1

HCID 59731041tert-Butyl 7-ethoxynaphthalen-1-ylcarbamate収率 67.5%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

Next, to a mixture of tert-butyl (7-hydroxy-1-naphthyl)carbamate (64.0 g, 247 mmol) and cesium carbonate (161 g, 493 mmol) in 300 mL anhydrous DMF was added iodoethane (42.3 g, 272 mmol) at room temperature. The mixture was stirred at 60° C. for 2 hours. Water was added to the mixture, and the product was extracted with ethylacetate. The organic layer was washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. To the obtained residue was added diisopropyl ether and the precipitate was collected and dried to afford tert-butyl (7-ethoxy-1-naphthyl)carbamate (47.9 g, 67.5% yield).

後処理

  1. extractionthe product was extracted with ethylacetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. additionTo the obtained residue was added diisopropyl ether
  7. customthe precipitate was collected
  8. customdried

出典と根拠

ORDレコード
ord-e1ce4d9ce19b46f2b5d1590c946e4e41
出典データセット
uspto-grants-2012_01
特許番号
US08088826B2

反応ノート

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