3,4-dihydro-2H-pyran → 2,2-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-propan-1-ol

HRID 1046437Notes

Reaction equation

HRID 1046437 reaction equation
[OH:1][CH2:2][C:3]([CH3:7])([CH2:5][OH:6])[CH3:4].[O:8]1[CH:13]=[CH:12][CH2:11][CH2:10][CH2:9]1.C([O-])(O)=O.[Na+]>CC1C=CC(S(O)(=O)=O)=CC=1.O.C1COCC1.ClCCl>[CH3:4][C:3]([CH3:7])([CH2:5][O:6][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][O:8]1)[CH2:2][OH:1]

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyranHCID 31344Neopentyl glycolHCID 516892Sodium Bicarbonate

Product 1

HCID 158113652,2-Dimethyl-3-(tetrahydro-pyran-2-yloxy)-propan-1-olYield 59%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

To a solution of neopentyl glycol (6.0 g, 57.6 mmol) and 3,4-dihydro-2H-pyran (2.64 mL, 28.94 mmol) in 2:1 THF/dichloromethane (135 mL) was added p-TsOH.H2O (100 mg, 0.53 mmol) and the reaction stirred overnight. Solid NaHCO3 was then added and after rapid stirring for 15 min the reaction was filtered and concentrated to give a pale liquid. Purification by flash column chromatography on silica gel using 50% ethyl acetate in hexanes provided 2,2-dimethyl-3-(tetrahydro-pyran-2-yloxy)-propan-1-ol (3.21 g, 59%) as a pale liquid.

Workup

  1. stirringafter rapid stirring for 15 min the reaction
  2. filtrationwas filtered
  3. concentrationconcentrated
  4. customto give a pale liquid
  5. customPurification by flash column chromatography on silica gel using 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-be8a505da71f4fa5affded154bef2693
Source dataset
uspto-grants-2013_10
Patent number
US08569302B2

Reaction notes

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