Tetrahydrofuran → HCID 54735985, compound

HRID 330271Notes

Reaction equation

HRID 330271 reaction equation
[H-].[Na+].C[O:4][C:5]1[C:6](=[CH:13][CH:14]=[CH:15][C:16]=1[Cl:17])[CH:7]=[CH:8][C:9]([O:11][CH3:12])=[O:10].C1C[O:21]CC1>>[C:9]([C:8]1[O:4][C:5]2[C:16]([Cl:17])=[CH:15][CH:14]=[CH:13][C:6]=2[C:7]=1[OH:21])([O:11][CH3:12])=[O:10]

Participants

4

Reactant 3

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 53641489HCID 53641489, compound

Product 1

HCID 54735985HCID 54735985, compoundYield 80%

Procedure

According to the procedure of D. C. Schroeder, et al., J. Org. Chem., 27, 586 (1962) to a stirred suspension of NaH (50% dispersion in mineral oil, washed with hexane) (4.5 g, 0.093 mol) in THF (20 mL) was added a solution of methyl (methyl 3-chlorosalicylyl)acetate (24.1 g, 0.093 mol) in THF (50 mL). Additional THF (60 mL) was added. After 1 hour, the mixture was heated under reflux for 1 hour, cooled, and partitioned between ether and H2O. The aqueous phase was acidified with 1N HCl and the precipitate was collected by filtration. This material was dissolved in ether. The solution was washed with H2O, dried (MgSO4), and concentrated to give a yellow solid (16.9 g, 80%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 1 hour
  3. temperaturecooled
  4. custompartitioned between ether and H2O
  5. filtrationthe precipitate was collected by filtration
  6. dissolutionThis material was dissolved in ether
  7. washThe solution was washed with H2O
  8. dry with materialdried (MgSO4)
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-1f78c9bb8c8543a0b63a199f5595fecb
Source dataset
uspto-grants-1990_01
Patent number
US04895860

Reaction notes

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