HCID 57659019, compound → 1-[(2R)-Tetrahydro-2-furanyl]-1-propanone

HRID 1669609Notes

Reaction equation

HRID 1669609 reaction equation
CON(C)[C:4]([C@H:6]1[CH2:10][CH2:9][CH2:8][O:7]1)=[O:5].[CH2:12]([Mg]Br)[CH3:13]>C1COCC1>[O:7]1[CH2:8][CH2:9][CH2:10][C@@H:6]1[C:4](=[O:5])[CH2:12][CH3:13]

Participants

4

Reactant 2

HCID 57659019HCID 57659019, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 670838321-[(2R)-Tetrahydro-2-furanyl]-1-propanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a cooled (0° C.) solution of (R)-N-methoxy-N-methyltetrahydrofuran-2-carboxamide (20.15 g, 1 equiv) in THF (250 ml) was added ethyl magnesium bromide (44.3 ml of a 3M solution in THF, 1.05 equiv) The reaction was stirred at −78° C. for 1 h and then quenched with saturated NH4Cl solution. EtOAc was added and the organic portion was separated and washed further with saturated NH4Cl solution, dried (MgSO4) and concentrated in vacuo to afford the title compound; NMR (CDCl3) 1.05 (3H, t, CH3), 1.9 (3H, m), 2.2 (1H, m, CH), 2.6 (2H, m, CH2), 3.95 (2H, CH2O), 4.3 (1H, m, CHO).

Workup

  1. customquenched with saturated NH4Cl solution
  2. additionEtOAc was added
  3. customthe organic portion was separated
  4. washwashed further with saturated NH4Cl solution
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-26d3f7af9e3c496da5b72dcb04a6db42
Source dataset
uspto-grants-2011_08
Patent number
US07989497B2

Reaction notes

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