Sodium Carbonate → 1-(4-Carboxyphenyl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)naphthalene

HRID 1276288ノート

反応式

HRID 1276288 の反応式
Br[C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[C:12]1[O:13][C:14]([CH3:17])=[N:15][N:16]=1.[C:18]([C:21]1[CH:26]=[CH:25][C:24](B(O)O)=[CH:23][CH:22]=1)([OH:20])=[O:19].C(=O)([O-])[O-].[Na+].[Na+]>C(COC)OC.O>[C:18]([C:21]1[CH:26]=[CH:25][C:24]([C:2]2[C:3]3[C:8](=[C:7]([C:12]4[O:13][C:14]([CH3:17])=[N:15][N:16]=4)[CH:6]=[CH:5][CH:4]=3)[CH:9]=[CH:10][CH:11]=2)=[CH:23][CH:22]=1)([OH:20])=[O:19]

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 3121834-Carboxyphenylboronic AcidHCID 221158772-(5-Bromo-1-naphthyl)-5-methyl-1,3,4-oxadiazole

生成物 1

HCID 221158831-(4-Carboxyphenyl)-5-(5-methyl-1,3,4-oxadiazol-2-yl)naphthalene

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

2-(5-Bromo-1-naphthyl)-5-methyl-1,3,4-oxadiazole (D3) (1.50 g, 5.2 mmol) and 4-carboxyphenylboronic acid (0.86 g, 5.2 mmol) were stirred in dimethoxyethane (DME) (40 ml), and sodium carbonate (2.5 g, 23 mmol) in water (40 ml) was added. The mixture was purged by a stream of Ar for 15 min, when tetrakis (triphenylphosphine)palladium (0) (0.1 g, 0.008 mmol) was added. The mixture was stirred at reflux under Ar for 20 h, and then evaporated to remove DME. The grey suspension was acidified (5M HCl), and the solid was filtered off and dried in vacuo at 60° C. This material was heated at reflux in ethanol (30 ml), and filtered hot. The white solid so collected was dried in vacuo at 60° C. giving 1.32 (77%) of the title compound.

後処理

  1. customThe mixture was purged by a stream of Ar for 15 min
  2. temperatureat reflux under Ar for 20 h
  3. customevaporated
  4. customto remove DME
  5. filtrationthe solid was filtered off
  6. customdried in vacuo at 60° C
  7. temperatureThis material was heated
  8. temperatureat reflux in ethanol (30 ml)
  9. filtrationfiltered hot
  10. customThe white solid so collected
  11. customwas dried in vacuo at 60° C.

出典と根拠

ORDレコード
ord-6c504619f122429baa9be1747df81230
出典データセット
uspto-grants-2000_12
特許番号
US06166034

反応ノート

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