3,4-dihydro-2H-pyran → HCID 69305305, compound

HRID 916888Notes

Reaction equation

HRID 916888 reaction equation
[OH:1][CH2:2][C:3]1[C:4](=[O:9])[CH2:5][CH2:6][C:7]=1[CH3:8].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.C(OCC)(=O)C>[CH3:8][C:7]1[CH2:6][CH2:5][C:4](=[O:9])[C:3]=1[CH2:2][O:1][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1

Participants

7

Reactant 4

HCID 80803,4-dihydro-2H-pyranHCID 516892Sodium BicarbonateHCID 521998p-Toluenesulfonic acid monohydrateHCID 157681462-(Hydroxymethyl)-3-methylcyclopent-2-en-1-one

Product 1

HCID 69305305HCID 69305305, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2-(hydroxymethyl)-3-methyl-2-cyclopentene-1-one (2.417 g, 19.16 mmol), prepared in example 14, was dissolved in methylene chloride (60 mL). Then, dihydropyran (4.02 g 47.9 mmol) and p-toluenesulfonic acid monohydrate (36 mg, 0.19 mmol) were added at room temperature. This solution was stirred for 2 hours, and then diluted with ethyl acetate (150 mL). The solution was neutralized with a saturated sodium bicarbonate solution (150 mL), and methylene chloride (200 mL) was added for extraction. After taking the organic layer, moisture was removed with magnesium sulfate, and the solvent was removed in vacuo. Pure 3-methyl-2-[(tetrahydropyranyloxy)methyl]-2-cyclopenten-1-one was obtained by column chromatography (hexane:ethyl acetate=1:1) (yield: 94%).

Workup

  1. additionwas added for extraction
  2. customwas removed with magnesium sulfate
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-a41071975e6a4d8f8a64d36dd123e3e3
Source dataset
uspto-grants-2007_09
Patent number
US07271277B2

Reaction notes

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