Ammonium Chloride → (3R,3aR,6R,6aS)-3-(5-fluoro-2-nitro-phenoxy)-6-methyl-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-6-ol

HRID 1396642ノート

反応式

HRID 1396642 の反応式
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[O:7][C@@H:8]1[CH2:12][O:11][C@@H:10]2[C:13](=[O:16])[CH2:14][O:15][C@H:9]12.[CH3:21][Li].[NH4+].[Cl-]>C1COCC1.C(OCC)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:18]([O-:20])=[O:19])=[C:6]([CH:17]=1)[O:7][C@@H:8]1[CH2:12][O:11][C@@H:10]2[C@:13]([CH3:21])([OH:16])[CH2:14][O:15][C@H:9]12

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 86718460(3R,3aR,6aS)-3-(5-fluoro-2-nitro-phenoxy)-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-oneHCID 178418348HCID 178418348、化合物

生成物 1

HCID 86718462(3R,3aR,6R,6aS)-3-(5-fluoro-2-nitro-phenoxy)-6-methyl-3,3a,5,6a-tetrahydro-2H-furo[3,2-b]furan-6-ol

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

1.6 g (5.7 mmol) (3R,3aR,6aS)-3-(5-fluoro-2-nitro-phenoxy)-2,3,3a,6a-tetrahydrofuro[3,2-b]furan-6-one (III.7) in THF are cooled to −70° C. 3.5 ml (5.7 mmol) 1.6 mol/l methyl lithium in diethyl ether are added dropwise and the reaction mixture is allowed to reach RT and stirred for 2.5 h. Aqueous NH4Cl solution and diethyl ether are added and the organic layer is separated, dried and evaporated. The residue is purified by FC (Al2O3).

後処理

  1. customto reach RT
  2. customthe organic layer is separated
  3. customdried
  4. customevaporated
  5. customThe residue is purified by FC (Al2O3)

出典と根拠

ORDレコード
ord-2c027ff4423e42bfa9b70c25e5197919
出典データセット
uspto-grants-2014_12
特許番号
US08901138B2

反応ノート

読み込み中…