Stannous chloride dihydrate → HCID 178473680, compound

HRID 1814747Notes

Reaction equation

HRID 1814747 reaction equation
[CH2:1]([O:3][P:4]([C:9]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=1)([O:12][CH2:13][CH3:14])[PH2:10]=[O:11])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2].O.O.Cl[Sn]Cl>CCO>[CH2:1]([O:3][P:4]([C:9]([C:15]1[CH:16]=[CH:17][C:18]([NH2:21])=[CH:19][CH:20]=1)([O:12][CH2:13][CH3:14])[PH2:10]=[O:11])(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]

Participants

4

Reactant 2

HCID 61436Stannous chloride dihydrateHCID 178473681HCID 178473681, compound

Product 1

HCID 178473680HCID 178473680, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of [(4-nitro-phenyl)-ethoxy-phosphinoylmethyl]-phosphonic acid diethyl ester (940 mg, 2.57 mmol) and SnCl2.2H2O (2.9 g, 12.9 mmol) in EtOH (˜10 mL) was stirred at 70° C. for 44 min and then concentrated at ambient temperature. The residue was taken up in CH2Cl2 and washed with half saturated aq NaHCO3 (40 mL), H2O (40 mL) and brine (40 mL). The aqueous washes were reextracted once with CH2Cl2, and the combined extracts were dried over K2CO3 and concentrated. The crude material was purified by flash chromatography on silica gel. Elution with 20:1 CHCl3-MeOH followed by 15:1 CHCl3-MeOH afforded 657 mg of product.

Workup

  1. concentrationconcentrated at ambient temperature
  2. washwashed with half saturated aq NaHCO3 (40 mL), H2O (40 mL) and brine (40 mL)
  3. dry with materialthe combined extracts were dried over K2CO3
  4. concentrationconcentrated
  5. customThe crude material was purified by flash chromatography on silica gel
  6. washElution with 20:1 CHCl3-MeOH

Sources & evidence

ORD record
ord-4d23c665ad6d4e5c96f017516be62ca6
Source dataset
uspto-grants-2005_04
Patent number
US06878697B2

Reaction notes

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