Diethyl Ether → 1-(Tetrahydro-2H-pyran-4-yl)ethanone

HRID 2088912Notes

Reaction equation

HRID 2088912 reaction equation
C[Mg]Br.[CH2:4](OCC)C.CON(C)[C:12]([CH:14]1[CH2:19][CH2:18][O:17][CH2:16][CH2:15]1)=[O:13]>O1CCCC1>[O:17]1[CH2:16][CH2:15][CH:14]([C:12](=[O:13])[CH3:4])[CH2:19][CH2:18]1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 23144693N-methoxy-N-methyloxane-4-carboxamideHCID 178418573HCID 178418573, compound

Product 1

HCID 98773651-(Tetrahydro-2H-pyran-4-yl)ethanoneYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add 3 M methyl magnesium bromide in diethyl ether (1.14 L, 2.0 eq) to a solution of N-methoxy-N-methyl-tetrahydropyran-4-carboxamide (296 g, 1.71 mol) in tetrahydrofuran (2.96 L) over one hour at 0° C. Stir for an additional two hours, then pour the contents into a mixture of ice/water. Extract with methyl tert-butyl ether. Dry the organics over anhydrous magnesium sulfate and concentrate in vacuo to give 1-(tetrahydro-pyran-4-yl)-ethanone (105 g, 48%). 1H NMR (300 MHz, DMSO-d6) δ 3.98 (m, 2H), 3.42 (m, 2H), 2.52 (m, 1H), 2.15 (s, 3H), 1.74 (m, 4H).

Workup

  1. additionpour the contents
  2. extractionExtract with methyl tert-butyl ether
  3. dry with materialDry the organics over anhydrous magnesium sulfate
  4. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-42095382887b4523947299ecb1ee6c9f
Source dataset
uspto-grants-2013_05
Patent number
US08436002B2

Reaction notes

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