Dicyclohexylcarbodiimide → HCID 54720229, compound

HRID 985416Notes

Reaction equation

HRID 985416 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][C:9]([OH:11])=[O:10].[C:12](OC)(=[O:16])[CH:13]([CH3:15])O.C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1.CN(C)C1C=CN=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:9](=[O:11])[O:10][CH:13]([CH3:15])[C:12]=1[OH:16]

Participants

6

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 11040Methyl LactateHCID 67979Benzeneacetic acid, 2-fluoro-

Product 1

HCID 54720229HCID 54720229, compoundYield 69.6%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To 2-fluorophenylacetic acid (25 g, 0.16 mol) and methyl lactate (17 g, 0.16 mol) in THF (600 ml) was added 1,3-dicyclohexylcarbodiimide (34 g, 0.16 mol) and 4-dimethylaminopyridine (0.99 g, 8.1 mmol) at 5° C. The mixture was allowed to warm to room temperature and stirred under nitrogen overnight. The solvent was removed in vacuo, then the residue was taken up in diethyl ether (300 ml), and the resulting slurry was filtered to remove insoluble material. The filtrate was concentrated in vacuo, and the residual oil was dissolved in potassium tert-butoxide solution (162 ml of a 1.0 M solution in tert-butanol). The mixture was stirred at reflux for 16 h and was allowed to cool to room temperature. Water (300 ml) was added, and the solution was washed with diethyl ether (2×100 ml). The aqueous solution was acidified to pH 1 with 5 N hydrochloric acid. The product formed an immiscible oil, which solidified upon standing. This was collected by filtration, washed with water and dried at 50° C., yielding 3-(2-fluorophenyl)-4-hydroxy-5-methyl-5H-furan-2-one as a pale yellow solid (23.2 g). 1H NMR (400 MHz, CDCl3) δ 1.46 (3H, d, J=6.7 Hz), 5.00 (1H, q, J=6.7 Hz), 7.22 (2H, m), 7.39 (2H, m), 12.50 (1H, br s).

Workup

  1. customThe solvent was removed in vacuo
  2. filtrationthe resulting slurry was filtered
  3. customto remove insoluble material
  4. concentrationThe filtrate was concentrated in vacuo
  5. dissolutionthe residual oil was dissolved in potassium tert-butoxide solution (162 ml of a 1.0 M solution in tert-butanol)
  6. stirringThe mixture was stirred
  7. temperatureat reflux for 16 h
  8. temperatureto cool to room temperature
  9. additionWater (300 ml) was added
  10. washthe solution was washed with diethyl ether (2×100 ml)
  11. customThe product formed an immiscible oil, which
  12. filtrationThis was collected by filtration
  13. washwashed with water
  14. customdried at 50° C.

Sources & evidence

ORD record
ord-9e20af205fd34ff79f5f4d374e8c66e8
Source dataset
uspto-grants-2005_03
Patent number
US06872720B2

Reaction notes

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