methyl 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propanoate → 2-Methyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]-1-propanol

HRID 2386268Notes

Reaction equation

HRID 2386268 reaction equation
[CH3:1][C:2]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)([CH3:7])[C:3](OC)=[O:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:7][C:2]([O:8][CH:9]1[CH2:14][CH2:13][CH2:12][CH2:11][O:10]1)([CH3:1])[CH2:3][OH:4]

Participants

4

Reactant 2

HCID 14892417methyl 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 242096552-Methyl-2-[(tetrahydro-2H-pyran-2-yl)oxy]-1-propanolYield 108.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propanoate (1.25 g, 6.16 mmol) in THF (20 ml) under nitrogen was added portionwise lithium aluminium hydride (0.246 g, 6.16 mmol) at 0° C. and the reaction mixture was stirred 2 h, followed by slow addition of Na2SO4.10H2O (1.98 g, 6.16 mmol). After 30 minutes of stirring at 0° C. to room temperature, the insoluble materials were filtered off. The filtrate was concentrated in vacuo to give 2-methyl-2-(tetrahydro-2H-pyran-2-yloxy)propan-1-ol (1.16 g, 6.68 mmol, quant.) as a colorless oil which was used in the next step without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.11 (s, 6H) 1.29-1.62 (m, 5H) 1.67-1.80 (m, 1H) 3.19-3.31 (m, 2H) 3.34-3.43 (m, 1H) 3.77-3.88 (m, 1H) 4.40 (t, J=5.94 Hz, 1H) 4.75-4.81 (m, 1H).

Workup

  1. stirringAfter 30 minutes of stirring at 0° C. to room temperature
  2. filtrationthe insoluble materials were filtered off
  3. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-63209ae405cb4dd4af962dc440bdeafe
Source dataset
uspto-grants-2012_09
Patent number
US08268819B2

Reaction notes

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