Cyclohexylamine → 2-Fluoro-5-nitrophenylhydroxymethylphosphonic acid

HRID 1604732ノート

反応式

HRID 1604732 の反応式
[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1C=O.C[Si]([O:17][P:18]([O:24][Si](C)(C)C)[O:19][Si](C)(C)C)(C)C.C1(N)CCCCC1.[O:36]1CCC[CH2:37]1>>[F:1][C:2]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][C:3]=1[O:17][P:18]([CH2:37][OH:36])(=[O:24])[OH:19]

参加物

5

反応物 4

HCID 7965CyclohexylamineHCID 8028TetrahydrofuranHCID 137213Tris(trimethylsilyl) phosphiteHCID 27347702-Fluoro-5-nitrobenzaldehyde

生成物 1

HCID 867548802-Fluoro-5-nitrophenylhydroxymethylphosphonic acid

実験手順

2-Fluoro-5-nitrobenzaldehyde (1.75 g, 10.0 mmol) was dissolved in tetrahydrofuran(50 mL). Tris(trimethylsilyl)phosphite (3.45 mL, 10.0 mmol) was added. The reaction mixture was stirred for 2.5 hours. Evaporation gave an oil which was dissolved in ethanol-ether. Addition of cyclohexylamine (1.14 mL,10.0 mmol) gave a solid salt which was filtered. Recrystallization from water gave 1.88 g (53.0%) of analytically pure product, mp 226-231° C.1H NMR (DMSO): d, 8.47 (m,1H), 8.11 (m,1H), 7.34 (t,1H), 4.85 (d,1H). MS (neg FAB): 249.9 (M-H). C7H7FNO6P/C6H13N.

後処理

  1. customEvaporation
  2. customgave an oil which
  3. customgave a solid salt which
  4. filtrationwas filtered
  5. customRecrystallization from water
  6. customgave 1.88 g (53.0%) of analytically pure product, mp 226-231° C

出典と根拠

ORDレコード
ord-d69da30bdfc844c8b1ce6a7cf18b2ca6
出典データセット
uspto-grants-1999_11
特許番号
US05994563

反応ノート

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