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

HRID 2192721Notes

Reaction equation

HRID 2192721 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-29b4380bc71b4b4d90847551a1bc9959
Source dataset
uspto-grants-2012_12
Patent number
US08329754B2

Reaction notes

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