Pyridine → HCID 57794586, compound

HRID 2099819Notes

Reaction equation

HRID 2099819 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:23])[CH3:22]>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:23])[CH3:22]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 3780918DiethylphosphiteHCID 15620607Glyoxylic acid, monohydrate

Product 1

HCID 57794586HCID 57794586, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

Glyoxylic acid monohydrate (4.00 g, 43.45 mmol) was suspended in diethyl phosphite (5.59 mL, 1.0 equiv) and warmed to 60° C. for 5 h. The reaction was cooled, diluted with dichloromethane (40 mL), and treated with pyridine (3.51 mL, 1.0 equiv) and acetyl chloride (3.09 mL, 1.0 equiv). A significant exotherm was noted. The reaction was stirred at room temperature for 2 h. The reaction was washed with 1 M hydrochloric acid (2×20 mL), then saturated sodium bicarbonate. The organics were dried over magnesium sulfate, and concentrated to give <2 g as an oil. The aqueous washes were combined and extracted with dichloromethane (4×). The organics were dried over magnesium sulfate and concentrated to give 5.85 g (53%) as an oil which solidified upon standing. 1H-NMR (CDCl3, 500 MHz) δ 1.36 (t, J=7.0, 6H), 2.21 (s, 3H), 4.28 (m, 4H), 5.54 (d, J=17.7, 1H), 8.90 (bs, 1H). Mass spec.: 255.10 (MH)+.

Workup

  1. temperatureThe reaction was cooled
  2. washThe reaction was washed with 1 M hydrochloric acid (2×20 mL)
  3. dry with materialThe organics were dried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give <2 g as an oil
  6. extractionextracted with dichloromethane (4×)
  7. dry with materialThe organics were dried over magnesium sulfate
  8. concentrationconcentrated
  9. customto give 5.85 g (53%) as an oil which

Sources & evidence

ORD record
ord-df52a87c12db4f32a78608de91ae5886
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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