Tetrahydrofuran → HCID 22881900, compound

HRID 861336Notes

Reaction equation

HRID 861336 reaction equation
[O:1]([CH2:8][CH2:9][CH2:10][C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[O:18]1[CH2:22][CH2:21][NH:20][C:19]1=[O:23].[CH2:24]([Li])[CH2:25][CH2:26][CH3:27].[CH2:29]1[CH2:33]OC[CH2:30]1>>[O:1]([CH2:8][CH2:9][CH2:10][C:11]([N:20]1[C@@H:21]([CH2:27][C:26]2[CH:33]=[CH:29][CH:30]=[CH:24][CH:25]=2)[CH2:22][O:18][C:19]1=[O:23])=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 5

HCID 8028TetrahydrofuranHCID 227414-Phenoxybutyric acidHCID 24386Thionyl ChlorideHCID 739492-OxazolidinoneHCID 178418339Butyllithium

Product 1

HCID 22881900HCID 22881900, compound

Procedure

4-Phenoxybutyric acid (1.22 g, 6.8 mmol, 1.2 equiv) was heated to reflux with thionyl chloride (0.66 ml, 1.07 g, 9.0 mmol, 1.6 equiv) for 30 min. The excess thionyl chloride was then removed under vacuum, the residue dissolved in THF (10 ml), and added to a cold (-78° C.) solution of lithiated (S)-4-benzyl-2-oxazolidinone [prepared from the oxazolodinone (1 g, 5.6 mmol) and n-butyllithium (1.6M solution, 4.23 ml, 6.8 mmol, 1.2 equiv) in THF (25 ml)]. The reaction mixture was stored for 2 hr at -78° C., then quenched with a 1:1 mixture of saturated brine and 10% HCI acid (20 ml). The mixture was allowed to warm to RT and partitioned between ethyl acetate and water. The layers were separated and the aqueous layer washed twice with ethyl acetate. The combined organic layers were washed once with brine, once with sodium bicarbonate solution, dried (MgSO4) and the solvent removed under vacuum to give a brown oil which was recrystallised (ethyl acetate) to give the title compound (0.897 g) as a white solid. δH (CDCl3) 7.35-7.17 (m, 7H), 6.94-6.86 (m, 3H), 4.66 (m, 1H), 4.18 (m, 2H), 4.06 (t, 2H), 3.30 (dd, 1H), 3.16 (t, 2H 2.25 (dd, 1H), and 2.18 (m, 2H).

Workup

  1. customThe excess thionyl chloride was then removed under vacuum
  2. dissolutionthe residue dissolved in THF (10 ml)
  3. additionadded to a cold (-78° C.) solution of lithiated (S)-4-benzyl-2-oxazolidinone [
  4. customquenched with a 1:1 mixture of saturated brine and 10% HCI acid (20 ml)
  5. custompartitioned between ethyl acetate and water
  6. customThe layers were separated
  7. washthe aqueous layer washed twice with ethyl acetate
  8. washThe combined organic layers were washed once with brine, once with sodium bicarbonate solution
  9. dry with materialdried (MgSO4)
  10. customthe solvent removed under vacuum
  11. customto give a brown oil which
  12. customwas recrystallised (ethyl acetate)

Sources & evidence

ORD record
ord-0d1b6f6702704ba49784b0cc25ab92fb
Source dataset
uspto-grants-1998_02
Patent number
US05714491

Reaction notes

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