Water → methyl 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propanoate

HRID 2386267Notes

Reaction equation

HRID 2386267 reaction equation
[OH:1][C:2]([CH3:8])([CH3:7])[C:3]([O:5][CH3:6])=[O:4].[O:9]1[CH:14]=[CH:13][CH2:12][CH2:11][CH2:10]1.O>ClCCl.CC1C=CC(S(O)(=O)=O)=CC=1.N1C=CC=CC=1>[CH3:7][C:2]([O:1][CH:10]1[CH2:11][CH2:12][CH2:13][CH2:14][O:9]1)([CH3:8])[C:3]([O:5][CH3:6])=[O:4]

Participants

6

Reactant 3

HCID 962WaterHCID 80803,4-dihydro-2H-pyranHCID 75024Methyl alpha-hydroxyisobutyrate

Product 1

HCID 14892417methyl 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propanoateYield 85%

Reagents, catalysts & solvents 2

HCID 161440Pyridine 4-methylbenzene-1-sulfonateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a mixture of methyl 2-hydroxy-2-methylpropanoate (5.04 g, 42.7 mmol) and 3,4-dihydro-2H-pyran (5.85 ml, 64.0 mmol) in dichloromethane (40 ml) was added pyridine 4-methylbenzenesulfonate (0.536 g, 2.13 mmol) and the reaction mixture was stirred for 1.5 hours. The reaction mixture was poured into water and extracted with Et2O. The organic layers were dried over Na2SO4 filtered, and concentrated in vacuo to give a crude oil. The crude residue was purified by silica gel chromatography (hexane/ethyl acetate, 100:0 to 17:3) to afford methyl 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propanoate (7.30 g, 36.1 mmol, 85% yield) as a colorless oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.35 (s, 3H) 1.36-1.55 (m, 7H) 1.57-1.81 (m, 2H) 3.32-3.42 (m, 1H) 3.62 (s, 3H) 3.72-3.85 (m, 1H) 4.65-4.75 (m, 1H).

Workup

  1. extractionextracted with Et2O
  2. dry with materialThe organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a crude oil
  6. customThe crude residue was purified by silica gel chromatography (hexane/ethyl acetate, 100:0 to 17:3)

Sources & evidence

ORD record
ord-d7d8f624fd844785915839935b3e87cf
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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