Tetrahydrofuran → HCID 59309639、化合物

HRID 1512970ノート

反応式

HRID 1512970 の反応式
[Cl:1][C:2]1[C:3]([N+:22]([O-])=O)=[CH:4][C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[C:6]([O:8][CH3:9])[CH:7]=1.O1CCCC1.[BH4-].[Na+].C(=O)([O-])O.[Na+]>[Ni](Br)Br.CO>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[C:5]([O:10][CH2:11][C:12]2[C:17]([O:18][CH3:19])=[CH:16][CH:15]=[C:14]([F:20])[C:13]=2[F:21])=[CH:4][C:3]=1[NH2:22]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 593097415-Chloro-2-(2,3-difluoro-6-methoxybenzyloxy)-4-nitroanisole

生成物 1

HCID 59309639HCID 59309639、化合物収率 90.1%

試薬・触媒・溶媒 2

HCID 278492Nickel(II) bromide触媒HCID 887Methanol溶媒

実験手順

To a mixture of 5-chloro-2-(2,3-difluoro-6-methoxybenzyloxy)-4-nitroanisole (9.41 g), nickel(II) bromide (0.29 g), tetrahydrofuran (100 mL) and methanol (100 mL) was added sodium borohydride (2.97 g) under ice-cooling, and the mixture was stirred under ice-cooling for 30 minutes, and then stirred at room temperature for 30 minutes. To the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethyl acetate. The extract was washed with brine twice, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1-3/2) to give the title compound (7.77 g).

後処理

  1. temperaturecooling
  2. temperaturecooling for 30 minutes
  3. stirringstirred at room temperature for 30 minutes
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe extract was washed with brine twice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=4/1-3/2)

出典と根拠

ORDレコード
ord-28cbfbd2958d4096bf3297721378fef3
出典データセット
uspto-grants-2012_07
特許番号
US08217069B2

反応ノート

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