Boron trifluoride etherate → 4-(3,4-Dinitrobenzyl)morpholine

HRID 1012091ノート

反応式

HRID 1012091 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([C:13]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)=O)[CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])([O-:3])=[O:2].[BH4-].[Na+].B(F)(F)F.CCOCC>C1COCC1>[N+:1]([C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][C:9]=1[N+:10]([O-:12])=[O:11])[CH2:13][N:15]1[CH2:20][CH2:19][O:18][CH2:17][CH2:16]1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 8000Boron trifluoride etherateHCID 4311764Sodium borohydrideHCID 13043973(3,4-Dinitrophenyl)(morpholino)methanone

生成物 1

HCID 251933104-(3,4-Dinitrobenzyl)morpholine収率 40%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a mixture of (3,4-dinitro-phenyl)-morpholin-4-yl-methanone (2.84 g) in dry THF (50 ml) was added NaBH4 (954 mg) followed drop-wise by BF3.Et2O (3.2 ml). The mixture was stirred at ambient temperature for 3 hours and then quenched though addition of MeOH. The mixture was reduced in vacuo, partitioned between EtOAc and water and the organic portion washed with brine, dried (MgSO4) and reduced in vacuo. The residue was purified via flash column chromatography eluting with EtOAc to give 4-(3,4-dinitro-benzyl)-morpholine (1.08 g).

後処理

  1. customquenched though addition of MeOH
  2. custompartitioned between EtOAc and water
  3. washthe organic portion washed with brine
  4. dry with materialdried (MgSO4)
  5. customThe residue was purified via flash column chromatography
  6. washeluting with EtOAc

出典と根拠

ORDレコード
ord-c1684d9900e74d9ca012f2f2a2c07c9f
出典データセット
uspto-grants-2011_07
特許番号
US07977477B2

反応ノート

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