Ethanol → HCID 10926216, compound

HRID 975485Notes

Reaction equation

HRID 975485 reaction equation
[CH2:1]1CCC(N=C=NC2CCCCC2)C[CH2:2]1.[C:16]([O:20][C:21]([NH:23][CH2:24][P:25]([CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])(=[O:27])[OH:26])=[O:22])([CH3:19])([CH3:18])[CH3:17].C(O)C>C1COCC1>[C:16]([O:20][C:21]([NH:23][CH2:24][P:25]([CH2:28][NH:29][C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])(=[O:26])[O:27][CH2:1][CH3:2])=[O:22])([CH3:19])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 702EthanolHCID 10868DicyclohexylcarbodiimideHCID 11120883HCID 11120883, compound

Product 1

HCID 10926216HCID 10926216, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

DCC (190 mg, 0.92 mmol) in THF (4 ml) is added dropwise in the course of 4 minutes to a solution of the phosphinic acid 1 (270 mg, 0.83 mmol) in dry THF (4 ml) and abs. ethanol (0.30 ml, 5.15 mmol) which is boiling under reflux. After 1.5 hours (checking by TLC), the reaction solution is cooled to room temperature and filtered. The filter residue is washed with ether. The filtrate is extracted with water (2×20 ml). The organic phase is dried over Na2SO4 and concentrated under reduced pressure. After purification by column chromatography on silica gel (ethyl acetate/heptane=3:2), the phosphinic acid ester 3 (100 mg, 34% of theory) is obtained. M.p. 117.5°-120° C.

Workup

  1. temperatureunder reflux
  2. filtrationfiltered
  3. washThe filter residue is washed with ether
  4. extractionThe filtrate is extracted with water (2×20 ml)
  5. dry with materialThe organic phase is dried over Na2SO4
  6. concentrationconcentrated under reduced pressure
  7. customAfter purification by column chromatography on silica gel (ethyl acetate/heptane=3:2)

Sources & evidence

ORD record
ord-9d1fc4e457ae408b999b6b820f27140f
Source dataset
uspto-grants-1997_03
Patent number
US05608098

Reaction notes

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