3,4-dihydro-2H-pyran → HCID 58922294, compound

HRID 1034573Notes

Reaction equation

HRID 1034573 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[C:8](=[O:13])[CH2:9][CH:10]([OH:12])[CH:11]=1)=[O:5])[CH3:2].[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1>ClCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH2:1]([O:3][C:4]([CH2:6][C:7]1[C:8](=[O:13])[CH2:9][CH:10]([O:12][CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][O:14]2)[CH:11]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 14223298HCID 14223298, compound

Product 1

HCID 58922294HCID 58922294, compoundYield 95.1%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

100 g of 2-ethoxycarbonylmethyl-4-hydroxy-2-cyclopenten-1-one was dissolved in 1000 ml dichloromethane, and added with 55 g of 3,4-dihydro-2H-pyran and 2 g of p-toluenesulfonic acid monohydrate, and then stirred at room temperature for about 3 hours. Upon completion of the reaction, the reaction mixture was washed with 400 ml of a saturated aqueous sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and concentrated to obtain 2-ethoxycarbonylmethyl-4-tetrahydropyranyloxy-2-cyclopenten-1-one (138.5 g). 1H-NMR (CDCl3/TMS): δ 7.40-7.68 (m, 1H), 4.70˜5.02 (m, 2H), 4.15 (q, 2H), 3.88 (m, 1H), 3.54 (m,1H), 3.23 (q, 2H), 2.79 (m,1H), 2.37 (m, 1H), 1.77 (m, 2H), 1.55 (m, 4H), 1.25 (t, 3H).

Workup

  1. customUpon completion of the reaction
  2. washthe reaction mixture was washed with 400 ml of a saturated aqueous sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-b2f796a602804b4988e6a96307d49690
Source dataset
uspto-grants-2013_10
Patent number
US08546114B2

Reaction notes

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