Ethanol → HCID 10926216, compound

HRID 1721492Notes

Reaction equation

HRID 1721492 reaction equation
ClC(O[CH2:5][CH:6](C)C)=O.[C:9]([O:13][C:14]([NH:16][CH2:17][P:18]([CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:20])[OH:19])=[O:15])([CH3:12])([CH3:11])[CH3:10].C(O)C.C(N(CC)CC)C>C(Cl)Cl>[C:9]([O:13][C:14]([NH:16][CH2:17][P:18]([CH2:21][NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])(=[O:19])[O:20][CH2:5][CH3:6])=[O:15])([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 11120883HCID 11120883, compound

Product 1

HCID 10926216HCID 10926216, compoundYield 20.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Isobutyl chloroformate (1.50 ml; 11.48 mmol) is added dropwise and with stirring to a solution of the phosphinic acid 1 (3.200 g; 9.88 mmol) in a mixture of methylene chloride (50 ml), ethanol (3.00 ml; 51.59 mmol), triethylamine (1.40 ml; 10.06 mmol) and N,N-dimethylaminopyridine (10 mg) at 0° C. After 90 minutes the reaction solution is extracted with saturated aqueous ammonium chloride solution (30 ml) and saturated aqueous KHCO3 solution (30 ml). The organic phase is dried over Na2SO4 and evaporated under reduced pressure. The phosphinate 2 (700 mg, 20% of theory) is obtained after purification on silica gel, using column chromatography (ethyl acetate/heptane=3/2). Spectroscopic data is given above.

Workup

  1. extractionAfter 90 minutes the reaction solution is extracted with saturated aqueous ammonium chloride solution (30 ml) and saturated aqueous KHCO3 solution (30 ml)
  2. dry with materialThe organic phase is dried over Na2SO4
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fabc303a61ad4b9db5c5f72d8c7e555c
Source dataset
uspto-grants-1996_04
Patent number
US05510504

Reaction notes

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