Tetrahydrofuran → HCID 69589125, compound

HRID 1796857Notes

Reaction equation

HRID 1796857 reaction equation
[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([Li])[CH2:15][CH2:16]C.[CH2:19]1[CH2:23][O:22][CH2:21][CH2:20]1>>[CH2:1]([C@@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:21](=[O:22])[CH2:20][CH2:19][CH2:23][CH:15]([CH3:16])[CH3:14])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 2734969(R)-4-Benzyl-2-oxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 69589125HCID 69589125, compound

Conditions

Temperature
0 °C

Procedure

To a −78° C. solution of 4(R)-benzyl-2-oxazolidinone (21.28 g, 0.12 mol) in THF (360 mL) was added n-butyllithium (48 mL, 2.5M in hexane, 120 mmol). After 10 minutes Example 8A (19.76 g, 0.134 mol) was added. After 30 minutes the mixture was warmed to 0° C., and quenched with saturated ammonium chloride. The supernatant was decanted and concentrated. The residue was partitioned between water and ethyl acetate and the organic layer was washed sequentially with water, 1M sodium bicarbonate, water, and brine, dried (MgSO4), filtered, and concentrated to provide the desired product. MS (ESI) m/e 290 (M+H)+.

Workup

  1. customAfter 10 minutes
  2. customquenched with saturated ammonium chloride
  3. customThe supernatant was decanted
  4. concentrationconcentrated
  5. customThe residue was partitioned between water and ethyl acetate
  6. washthe organic layer was washed sequentially with water, 1M sodium bicarbonate, water, and brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-b1f9430cb36d411ea8b6a623c0325bb6
Source dataset
uspto-grants-2006_04
Patent number
US07030262B2

Reaction notes

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