Ethyl Acetate → HCID 12397257, compound

HRID 1606303Notes

Reaction equation

HRID 1606303 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:17]=[O:18])=[N:13][C:14]=1[CH2:15]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(OCC)(=O)C.P(Cl)(Cl)([Cl:27])=O>CCOCC>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:17]=[O:18])=[N:13][C:14]=1[CH2:15][Cl:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychloride2×HCID 12397256HCID 12397256, compound

Product 1

HCID 12397257HCID 12397257, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred solution of 5-benzyloxy-6-hydroxymethyl-2-pyridinecarboxaldehyde (5.86 g., 0.0241 mol) in 100 ml. of ethyl acetate is added 4.056 g. (0.0265 mol) of phosphorus oxychloride and the mixture is refluxed for 20 minutes. Additional phosphorus oxychloride (0.4 ml.) is introduced and the mixture is heated further for 30 minutes. The reaction mixture is cooled, diluted with ether and then washed with 5% sodium bicarbonate solution and brine. The ethereal solution is dried, treated with charcoal, filtered and evaporated to leave an oil which crystallizes to give 5-benzyloxy-6-chloromethyl-2-pyridinecarboxaldehyde, m.p. 72°-73°C.

Workup

  1. temperaturethe mixture is heated further for 30 minutes
  2. temperatureThe reaction mixture is cooled
  3. washwashed with 5% sodium bicarbonate solution and brine
  4. customThe ethereal solution is dried
  5. additiontreated with charcoal
  6. filtrationfiltered
  7. customevaporated
  8. customto leave an oil which
  9. customcrystallizes

Sources & evidence

ORD record
ord-12a0b8db854249c7a706d30cf3043b49
Source dataset
uspto-grants-1976_04
Patent number
US03952101

Reaction notes

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