Methanol → HCID 178502921, compound

HRID 976234Notes

Reaction equation

HRID 976234 reaction equation
[C:1]1([PH:7](=[O:9])[OH:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.[CH3:12]CN=C=NCCCN(C)C>CN(C)C1C=CN=CC=1.C1COCC1>[C:1]1([PH:7](=[O:8])[O:9][CH3:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 178527038HCID 178527038, compound

Product 1

HCID 178502921HCID 178502921, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of phenylphosphinic acid (5.00 g, 35.2 mmol), anhydrous methanol (7.0 mL, 170 mmol) and 4-dimethylaminopyridine (425 mg, 3.48 mmol) in 50 mL of THF (distilled from ketyl) was added EDAC (8.05 g, 42 mmol) at room temperature. The reaction was stirred for 24 hours then partitioned between HCl solution (75 mL of 1M aq) and ethyl acetate (75 mL). The organic layer was separated, washed with HCl solution (75 mL of 1M aq), sodium bicarbonate solution (75 mL of 5% aq) then dried (sodium sulfate) and concentrated in vacuo to afford the crude title compound as a colorless liquid (1.24 g, 7.95 mmol, 23%).

Workup

  1. customthen partitioned between HCl solution (75 mL of 1M aq) and ethyl acetate (75 mL)
  2. customThe organic layer was separated
  3. washwashed with HCl solution (75 mL of 1M aq), sodium bicarbonate solution (75 mL of 5% aq)
  4. dry with materialthen dried (sodium sulfate)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d51209eb6851464793a9a689f7af1883
Source dataset
uspto-grants-1997_03
Patent number
US05612323

Reaction notes

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