Triphenylphosphine → 2-(Azidomethyl)-5-(difluoromethyl)furan

HRID 2067338ノート

反応式

HRID 2067338 の反応式
[F:1][CH:2]([F:10])[C:3]1[O:7][C:6]([CH2:8]O)=[CH:5][CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(P([N:56]=[N+:57]=[N-:58])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1.ClCCl>[N:56]([CH2:8][C:6]1[O:7][C:3]([CH:2]([F:10])[F:1])=[CH:4][CH:5]=1)=[N+:57]=[N-:58]

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 5462977Diethyl azodicarboxylateHCID 20079677(5-(Difluoromethyl)furan-2-yl)methanol

生成物 1

HCID 866452892-(Azidomethyl)-5-(difluoromethyl)furan収率 77%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (5-(difluoromethyl)furan-2-yl)methanol (0.55 g, 3.72 mmol), triphenylphosphine (1.07 g, 4.09 mmol) and diethylazodicarboxylate (0.64 mL, 4.09 mmol) in anhydrous tetrahydrofuran (20 mL) was added diphenylphosphorylazide (0.88 mL, 4.09 mmol). The reaction mixture was stirred at ambient temperature for 18 hours, diluted with dichloromethane (40 mL) and washed with water and brine. The organic solution was dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography eluted with ethyl acetate/hexane (1/9) to afford 2-(azidomethyl)-5-(difluoromethyl)furan as a yellow oil in 77% yield (0.50 g): 1H NMR (300 MHz, CDCl3) δ 6.61 (d, J=3.3 Hz, 1H), 6.58 (t, J=54.3 Hz, 1H), 6.37 (d, J=3.3 Hz, 1H), 4.30 (s, 2H); MS (ES+) m/z 172.2 (M+1).

後処理

  1. washwashed with water and brine
  2. dry with materialThe organic solution was dried over anhydrous sodium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography
  6. washeluted with ethyl acetate/hexane (1/9)

出典と根拠

ORDレコード
ord-cff9a5fea9b342778c8633fd23e4199c
出典データセット
uspto-grants-2012_10
特許番号
US08293768B2

反応ノート

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