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

HRID 1934887Notes

Reaction equation

HRID 1934887 reaction equation
[Cl-].C([C@H:9]1[CH2:13][O:12][C:11](=[O:14])[N:10]1[C:15](=[O:36])[CH2:16]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C1C=CC=CC=1.[CH:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][C:38]=1[CH:47]=O.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.C(#N)C>[CH:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][C:38]=1/[CH:47]=[CH:16]/[C:15]([N:10]1[CH2:9][CH2:13][O:12][C:11]1=[O:14])=[O:36]

Participants

6

Reactant 3

HCID 62012-NaphthalenecarboxaldehydeHCID 8471TriethylamineHCID 178521517HCID 178521517, compound

Product 1

HCID 60344543-[(E)-3-naphthalen-2-ylprop-2-enoyl]-1,3-oxazolidin-2-oneYield 69.8%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of (4S)-4-benzyl-3-[(triphenylphosphino) acetyl]-1,3-oxazolidin-one chloride (10 mg, 0.193 mmol), 2-naphthaldehyde (30 mg, 0.193 mmol), triethylamine (0.030 ml, 0.212 mmol) and 4-(dimethylamino)pyridine in acetonitrile (5 ml) was heated under reflux for 24 h. After evaporation, the residue was dissolved in hexaneetherdichloromethane and chromatographed on flash silica eluting with hexane:ether 3:2 to give a white solid (36 mg, 52%) of 3-[(E)-3-Naphthalen-2-ylprop-2-enoyl]-1,3-oxazolidin-2-one. M/e 358 (MH+).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 24 h
  3. customAfter evaporation
  4. dissolutionthe residue was dissolved in hexaneetherdichloromethane
  5. customchromatographed on flash silica eluting with hexane:ether 3:2

Sources & evidence

ORD record
ord-5dcb44bb9b5944ee87fe0e0f536a6237
Source dataset
uspto-grants-2002_05
Patent number
US06384281B1

Reaction notes

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