Triethylamine → 3-[(E)-3-naphthalen-2-ylprop-2-enoyl]-1,3-oxazolidin-2-one

HRID 1934886Notes

Reaction equation

HRID 1934886 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[C:13]([OH:15])=O.C(N(CC)CC)C.C(Cl)(=O)C(C)(C)C.[O:30]1[CH2:34][CH2:33][NH:32][C:31]1=[O:35].C([Li])CCC>O1CCCC1.O>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1/[CH:11]=[CH:12]/[C:13]([N:32]1[CH2:33][CH2:34][O:30][C:31]1=[O:35])=[O:15]

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 739492-Oxazolidinone2×HCID 7358353-(Naphth-2-yl)acrylic acidHCID 178418339Butyllithium

Product 1

HCID 60344543-[(E)-3-naphthalen-2-ylprop-2-enoyl]-1,3-oxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (E)-3-(2-naphthyl)prop-2-enoic acid (10 g, 0.05 mole) at −78° C., was added triethylamine (8.42 ml, 0.06 mole) and pivaloyl chloride (7.5 ml, 0.06 mole). Stirring was continued for 1 hour. To a stirred solution of oxazolidinone (5.14 g, 0.06 mole) in dry tetrahydrofuran (200 ml) at −78° C. was added slowly n-butyl lithium (1.6M in hexanes, 38 ml, 0.06 mole). Stirred for 1 hour. The suspension of the mixed anhydride was transferred into the oxazolidinone anion by means of a canula maintaining the temperature below −60° C. The resulting reaction mixture was stirred for 2 hours. Water was added cautiously and the reaction extracted with ethyl acetate. The solvent was washed with brine, dried and evaporated to dryness in-vacuo. Chromatography on flash silica using ethyl acetatehexane (1:1) gave 3-[(E)-3-naphthalen-2-ylprop-2-enoyl]-1,3-oxazolidin-2-one as a white solid, M/e 268 (M+H).

Workup

  1. stirringStirred for 1 hour
  2. temperaturemaintaining the temperature below −60° C
  3. customThe resulting reaction mixture
  4. stirringwas stirred for 2 hours
  5. extractionthe reaction extracted with ethyl acetate
  6. washThe solvent was washed with brine
  7. customdried
  8. customevaporated to dryness in-vacuo

Sources & evidence

ORD record
ord-74c530d3ee68446f81e7075c8d68a4ea
Source dataset
uspto-grants-2002_05
Patent number
US06384281B1

Reaction notes

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