Hydrochloric Acid → HCID 11820489, compound

HRID 1940023Notes

Reaction equation

HRID 1940023 reaction equation
[OH:1][C:2]1[C:3](=[O:9])[CH:4]([CH3:8])[O:5][C:6]=1[CH3:7].[C:10](Cl)(=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12].Cl>CN(C)C1C=CN=CC=1.N1C=CC=CC=1.C(Cl)Cl>[CH3:7][CH:6]1[C:2](=[O:1])[C:3]([O:9][C:10](=[O:15])[C:11]([CH3:14])([CH3:13])[CH3:12])=[C:4]([CH3:8])[O:5]1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 19309FuraneolHCID 62493Pivaloyl chloride

Product 1

HCID 11820489HCID 11820489, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

4-Hydroxy-2,5-dimethyl-3(2H)-furanone (1.0 g, TOKYO KASEI KOGYO CO., LTD.) and 4-dimethylaminopyridine (0.05 g) were dissolved in a mixture solution of pyridine (10 ml) and methylene chloride (10 ml) under an argon stream in a 50 ml two-necked flask. To the resulting solution, pivaloyl chloride (1.06 ml) was added dropwise under cooling with ice and the mixture was stirred at room temperature for 1 hour. Subsequently, the reaction mixture solution was mixed with a 0.5N ice-cooled aqueous solution of HCl (10 ml) and subjected to extraction with diethyl ether (30 ml). The ether-extraction was repeated 3 times. The ether layer was washed 3 times with a 0.5N aqueous solution of HCl, twice with a saturated aqueous solution of sodium bicarbonate and once with a saturated saline solution and dried over sodium sulfate. The ether layer was then concentrated under a reduced pressure and applied to a silica gel column for separation and purification. Thus, 2,5-dimethyl-4-pivaloyloxy-3(2H)-furanone (1.40 g) was obtained.

Workup

  1. temperatureunder cooling with ice
  2. extractionsubjected to extraction with diethyl ether (30 ml)
  3. extractionThe ether-extraction
  4. washThe ether layer was washed 3 times with a 0.5N aqueous solution of HCl
  5. dry with materialtwice with a saturated aqueous solution of sodium bicarbonate and once with a saturated saline solution and dried over sodium sulfate
  6. concentrationThe ether layer was then concentrated under a reduced pressure
  7. customapplied to a silica gel column for separation and purification

Sources & evidence

ORD record
ord-21fbda972d0c449cb02f4ab673b0b4f4
Source dataset
uspto-grants-1997_12
Patent number
US05698585

Reaction notes

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