Sulfuric Acid → methyl 2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propanoate

HRID 469755Notes

Reaction equation

HRID 469755 reaction equation
[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][OH:6].[O:10]1[CH:15]=[CH:14][CH2:13][CH2:12][CH2:11]1.S(=O)(=O)(O)O>ClCCl>[CH3:1][O:2][C:3](=[O:9])[C:4]([CH3:8])([CH3:7])[CH2:5][O:6][CH:11]1[CH2:12][CH2:13][CH2:14][CH2:15][O:10]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 80803,4-dihydro-2H-pyranHCID 84152Methyl 3-hydroxypivalate

Product 1

HCID 59253280methyl 2,2-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)propanoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of hydroxypivalic acid methyl ester (4 mL, 31.36 mmol) in dichloromethane (20 mL) is added 3,4-dihydro-2H-pyran (5.84 mL, 63.99 mmol). The reaction mixture is cooled to 0° C. and sulfuric acid on silica gel (125 mg, 0.2 mL sulfuric acid/10 g silica gel) is added and the reaction mixture is stirred at room temperature for 25 minutes. After this time, the reaction mixture is filtered through a glass funnel and concentrated under reduced pressure to yield the title compound. It is used without purification.

Workup

  1. filtrationAfter this time, the reaction mixture is filtered through a glass funnel
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fcc1878ea45544198e365e8e15cfbc71
Source dataset
uspto-grants-2014_01
Patent number
US08629157B2

Reaction notes

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