Cyclohexylamine → 2-Fluoro-5-nitrophenylhydroxymethylphosphonic acid

HRID 1604732

반응식

HRID 1604732 반응식
[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]

참가 물질

5

반응물 4

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

생성물 1

HCID 867548802-Fluoro-5-nitrophenylhydroxymethylphosphonic acid

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-d69da30bdfc844c8b1ce6a7cf18b2ca6
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05994563

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