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

HRID 560565ノート

反応式

HRID 560565 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-1943ff4e88df4bb5bf7c745eea596efb
出典データセット
uspto-grants-2011_11
特許番号
US08063084B2

反応ノート

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