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 1396642노트

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HRID 1396642 반응식
[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

참가 물질

6

반응물 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, 화합물

생성물 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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매2회HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-2c027ff4423e42bfa9b70c25e5197919
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08901138B2

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