HCID 86589708, compound → HCID 86589707, compound

HRID 1357386Notes

Reaction equation

HRID 1357386 reaction equation
[CH2:1]([O:3][P:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[N+:22]([O-])=O)=[CH:11][CH:10]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>C(Cl)Cl.[Pd]>[CH2:6]([O:5][P:4]([C:9]1[CH:14]=[CH:13][C:12]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])=[CH:11][CH:10]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 1

HCID 86589708HCID 86589708, compound

Product 1

HCID 86589707HCID 86589707, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

[4-(2-Nitrophenoxy)phenyl]phosphonic acid diethyl ester (140 mg, 0.4 mmol) was dissolved in methylene chloride and Pd/C 10% was added under N2. The compound was reduced with H2 in a Parr-apparatus at 207 kPa (30 psi) for 15 hours. The catalyst was filtered off and the organic phase was evaporated in vacuo. The remaining oil was purified on a silica gel column (eluent: methylene chloride/methanol (39.1)) to give the title compound as an oil (yield: 118 mg (92%)). 1H—NMR (CDCl3(in ppm: 1.32 (6H,t); 3.8 (2H,broad s); 4.1 (4H,q); 6.7 (1H,d.t.); 6.85 (1H,d.d.); 6.9 (1H,d.d.); 7.0 (3H,m); 7.7 (1H, d); 7.85 (1H,d). 13C—NMR (CDCl3) in ppm: 16.7 16.8; 62,4; 62,5; 116.5; 116.8; 117.2; 119.2; 119.9; 121.7; 123.8; 126.4; 134.2; 134.4; 139.5; 141.8; 161.6; 161.6.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe organic phase was evaporated in vacuo
  3. customThe remaining oil was purified on a silica gel column (eluent: methylene chloride/methanol (39.1))

Sources & evidence

ORD record
ord-a27ab1dc8a1c43e09a059879bba66d46
Source dataset
uspto-grants-2003_07
Patent number
US06590118B1

Reaction notes

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