1-(Benzyloxy)-3-chloropropan-2-one → 3-(3-Benzyloxy-2-oxo-propyl)-5-methyl-1,3,4-oxadiazol-2-one

HRID 570906Notes

Reaction equation

HRID 570906 reaction equation
[Na].[CH3:2][C:3]1[O:7][C:6](=[O:8])[NH:5][N:4]=1.[CH2:9]([O:16][CH2:17][C:18](=[O:21])[CH2:19]Cl)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1>CN(C=O)C.O.[Cl-].[Na+].O>[CH2:9]([O:16][CH2:17][C:18](=[O:21])[CH2:19][N:5]1[N:4]=[C:3]([CH3:2])[O:7][C:6]1=[O:8])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

6

Reactant 2

HCID 111832331-(Benzyloxy)-3-chloropropan-2-oneHCID 896018065-Methyl-1,3,4-oxadiazol-2-one sodium salt

Product 1

HCID 896020683-(3-Benzyloxy-2-oxo-propyl)-5-methyl-1,3,4-oxadiazol-2-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a stirred suspension of 5-methyl-1,3,4-oxadiazol-2-one sodium salt (34.6 g, 284 mmol) in DMF (200 mL) at 0° C. was added dropwise a solution of 1-benzyloxy-3-chloro-propan-2-one (56.4 g, 284 mmol) in DMF (80 mL). After completion of the addition, the reaction mixture was allowed to warm to room temperature and stirring was continued for 16 h. The obtained reaction mixture was diluted with water and brine and extracted with EtOAc. The combined organic layers were washed with water, brine, and dried (Na2SO4). After evaporation of the solvent the desired product was obtained as a brown oil. Purification by flash chromatography (25% EtOAc/heptane) furnished the desired product as a yellowish oil. 1H NMR (400 MHz, CDCl3) 2.27 (s, 3H), 4.27 (s, 2H), 4.62 (s, 2H), 4.75 (s, 2H), 7.30-7.46 (m, 5H).

Workup

  1. additionAfter completion of the addition
  2. customThe obtained reaction mixture
  3. extractionextracted with EtOAc
  4. washThe combined organic layers were washed with water, brine
  5. dry with materialdried (Na2SO4)
  6. customAfter evaporation of the solvent the desired product
  7. customwas obtained as a brown oil
  8. customPurification by flash chromatography (25% EtOAc/heptane)

Sources & evidence

ORD record
ord-334d5b00e2ca47678a28727b5f0aeed7
Source dataset
uspto-grants-2015_05
Patent number
US09024019B2

Reaction notes

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