Ethyl Acetate → (S)-4-tert-butyldimethylsilyloxy-2-cyclopenten-1-one

HRID 1987537Notes

Reaction equation

HRID 1987537 reaction equation
[OH:1][C@H:2]1[CH2:6][C:5](=[O:7])[CH:4]=[CH:3]1.CN(CC)C.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].C(OCC)(=O)C>C(Cl)Cl>[CH3:17][C:16]([Si:13]([CH3:15])([CH3:14])[O:7][C@H:5]1[CH2:6][C:2](=[O:1])[CH:3]=[CH:4]1)([CH3:19])[CH3:18]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11723DimethylethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 1247114-Hydroxy-2-cyclopentenone

Product 1

HCID 10176717(S)-4-tert-butyldimethylsilyloxy-2-cyclopenten-1-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 1-L round bottomed flask was charged (4S)-4-Hydroxy-2-cyclopenten-1-one (32) (20 g, 204 mmol, prepared described in Khanapure, S.; Najafi, N.; Manna, S.; Yang, J.; Rokash. J. J. Org. Chem., 1995, 60, 7448) in DCM (200 mL) followed by N,N-dimethylethylamine (47.7 g, 653 mmol), tert-butyldimethylsilyl chloride (46.1 g, 306 mmol) and a catalytic amount of 4-N,N-dimethylaminopyridine (1 g). The mixture was stirred at room temperature for 24 hours. The reaction mixture was poured into ethyl acetate (200 mL) and the organic layer washed with water (200 mL), aqueous HCl (1 N, 2×100 mL), brine (100 mL) and saturated sodium bicarbonate solution (100 mL). The organic layer was dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a crude product (42 g, ˜98% yield).

Workup

  1. washthe organic layer washed with water (200 mL), aqueous HCl (1 N, 2×100 mL), brine (100 mL) and saturated sodium bicarbonate solution (100 mL)
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d345904494d84b849f04f273bb528ef2
Source dataset
uspto-grants-2009_06
Patent number
US07550619B2

Reaction notes

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