Pyridine → HCID 15364541, compound

HRID 501940Notes

Reaction equation

HRID 501940 reaction equation
O.[C:2]([OH:6])(=[O:5])[CH:3]=[O:4].[P:7]([O-:14])([O:11][CH2:12][CH3:13])[O:8][CH2:9][CH3:10].N1C=CC=CC=1.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>ClCCl>[C:21]([O:4][CH:3]([P:7]([O:11][CH2:12][CH3:13])([O:8][CH2:9][CH3:10])=[O:14])[C:2]([OH:6])=[O:5])(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 7412Benzoyl chlorideHCID 3780918DiethylphosphiteHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 15364541HCID 15364541, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Glyoxylic acid monohydrate (20.10 g, 218 mmol) was suspended in diethyl phosphite (28.1 mL, 1.0 equiv) and warmed to 60° C., and held there for 5 h. The reaction was cooled to 0° C., diluted with dichloromethane (200 mL), and treated with pyridine (17.7 mL, 1.0 equiv) and benzoyl chloride (25.3 mL, 1.0 equiv). The ice bath was removed and stirring continued overnight. The reaction was concentrated, diluted with ethyl acetate, washed with water, then 1M potassium bisulfate, then brine, dried over magnesium sulfate, and concentrated to give an oil. The oil was triturated with ether to give a white powder which was filtered, washed with diethyl ether, and air dried to give 29.0 g (42%). 1H-NMR (CDCl3, 500 MHz) δ 1.35 (m, 6H), 4.31 (m, 4H), 5.82 (d, J=17.7, 1H), 7.46 (m, 2H), 7.60 (m, 1H), 7.94 (bs, 1H), 8.12 (m, 2H).

Workup

  1. temperatureThe reaction was cooled to 0° C.
  2. customThe ice bath was removed
  3. concentrationThe reaction was concentrated
  4. additiondiluted with ethyl acetate
  5. washwashed with water
  6. dry with material1M potassium bisulfate, then brine, dried over magnesium sulfate
  7. concentrationconcentrated
  8. customto give an oil
  9. customThe oil was triturated with ether
  10. customto give a white powder which
  11. filtrationwas filtered
  12. washwashed with diethyl ether, and air
  13. customdried
  14. customto give 29.0 g (42%)

Sources & evidence

ORD record
ord-4df3446481564690891aba5578c19141
Source dataset
uspto-grants-2010_08
Patent number
US07772244B2

Reaction notes

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