Nitrogen → HCID 22025594、化合物

HRID 396594ノート

反応式

HRID 396594 の反応式
N#N.Br[C:4]1[C:5]([O:13][CH3:14])=[CH:6][C:7]([OH:12])=[C:8]([CH:11]=1)[CH:9]=[O:10].[S:15]1[CH:19]=[CH:18][CH:17]=[C:16]1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>COCCOC>[S:15]1[C:19]([C:4]2[C:5]([O:13][CH3:14])=[CH:6][C:7]([OH:12])=[C:8]([CH:11]=2)[CH:9]=[O:10])=[CH:18][C:17]2[CH:5]=[CH:4][CH:11]=[CH:8][C:16]1=2

参加物

6

反応物 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 8181085-Bromo-2-hydroxy-4-methoxybenzaldehydeHCID 27339602-Thiopheneboronic acid

生成物 1

HCID 22025594HCID 22025594、化合物収率 170.1%

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒

実験手順

Ex-62B: A stream of N2 was bubbled through a solution of 5-bromo-2-hydroxy-4-methoxybenzaldehyde (1 g, 4.3 mmol) from Ex-62A in 30 mL of ethylene glycol dimethyl ether for 15 min. Tetrakis-triphenylphosphine palladium (0) (0.5 g, 0.4 mmol) was added along with thiophene-2-boronic acid (1.2 g, 6.5 mmol) and 10 mL of Na2CO3 (2M aqueous solution). The resulting mixture was stirred under reflux overnight. The solvent was removed by rotary evaporation and the residue was treated with saturated NaHCO3 and extracted with dichloromethane. The organic phase was washed with brine, dried over MgSO4, and filtered to remove drying agent. Solvent was removed by rotary evaporation. Purification of the crude material by silica gel chromatography (hexanes/EtOAc, 2:1) gave 1.04 g of the desired 5-benzo[b]thien-2-yl-2-hydroxy-4-methoxybenzaldehyde.

後処理

  1. temperatureunder reflux overnight
  2. customThe solvent was removed by rotary evaporation
  3. additionthe residue was treated with saturated NaHCO3
  4. extractionextracted with dichloromethane
  5. washThe organic phase was washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customto remove
  9. customdrying agent
  10. customSolvent was removed by rotary evaporation
  11. customPurification of the crude material by silica gel chromatography (hexanes/EtOAc, 2:1)

出典と根拠

ORDレコード
ord-6d24c9270c8444baa03a6173ce021793
出典データセット
uspto-grants-2003_08
特許番号
US06608101B1

反応ノート

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