Boron trifluoride etherate → 2-(4-Chloro-2-methylphenoxymethyl)-3-methyl-4-oxazolidinone

HRID 461285Notes

Reaction equation

HRID 461285 reaction equation
B(F)(F)F.CCOCC.[Cl:10][C:11]1[CH:20]=[CH:19][C:14]([O:15][CH2:16][CH:17]=[O:18])=[C:13]([CH3:21])[CH:12]=1.[CH3:22][NH:23][C:24](=[O:27])[CH2:25]O>O1CCCC1>[Cl:10][C:11]1[CH:20]=[CH:19][C:14]([O:15][CH2:16][CH:17]2[N:23]([CH3:22])[C:24](=[O:27])[CH2:25][O:18]2)=[C:13]([CH3:21])[CH:12]=1

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 2235792-Hydroxy-N-methylacetamideHCID 123914592-(4-Chloro-2-methylphenoxy)acetaldehyde

Product 1

HCID 123914932-(4-Chloro-2-methylphenoxymethyl)-3-methyl-4-oxazolidinoneYield 11%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.6 g (0.0325 mole) of boron trifluoride etherate was added to a solution containing 4.6 g (0.025 mole) of (4-chloro-2-methylphenoxy)acetaldehyde and 2.5 g (0.028 mole) of N-methylglycolamide in 40 ml of tetrahydrofuran. After 24 hours at ambient temperature, the reaction mixture was concentrated under reduced pressure, extracted with ether, washed with water and dried. Purification by silica chromatography gave 0.7 g of 2-(4-chloro-2-methylphenoxymethyl)-3-methyl-4-oxazolidinone as a light yellow oil.

Workup

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with ether
  3. washwashed with water
  4. customdried
  5. customPurification by silica chromatography

Sources & evidence

ORD record
ord-8691e936157a42a4bc5f2f957447cd70
Source dataset
uspto-grants-1977_12
Patent number
US04062670

Reaction notes

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