Hydrochloric Acid → HCID 69640946, compound

HRID 1830579Notes

Reaction equation

HRID 1830579 reaction equation
[H-].[Na+].[C:3]([O:11]CC)(=[O:10])[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].C=C1OC(=O)C1.Cl.[O:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1>>[OH:21][C:25]1[CH:24]=[C:23]([CH3:22])[O:11][C:3](=[O:10])[C:4]=1[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 7761Diethyl MalonateHCID 8028Tetrahydrofuran2×HCID 12661DiketeneHCID 24758Sodium hydride

Product 1

HCID 69640946HCID 69640946, compound

Procedure

8 g of sodium hydride (ca. 60% in oil) was suspended in 200 ml of tetrahydrofuran, and 32 g of diethyl malonate was added dropwise with cooling on ice, and then stirred for 1 hour at room temperature. A solution of 14 g of a diketene in 30 ml of tetrahydrofuran was added dropwise to the reaction mixture with cooling on ice, and then the reaction mixture was stirred for 16 hours at room temperature. Subsequently, 1% hydrochloric acid was poured into the reaction mixture and the reaction mixture was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chrolide, dried over anhydrous magnesium sulfate, and then concentrated. The residue was subjected to a silica gel column chromatography to obtain 9.5 g of ethyl 4-hydroxy-6-methyl-2-oxo-2H-pyrane-3-carboxylate (Compound No. 1).

Workup

  1. temperaturewith cooling on ice
  2. temperaturewith cooling on ice
  3. stirringthe reaction mixture was stirred for 16 hours at room temperature
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chrolide
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8fd31ad07dcb44c099f42da8d5eb611a
Source dataset
uspto-grants-2006_06
Patent number
US07067523B2

Reaction notes

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