Benzene → 3-Methyl-3-oxetanylmethyl 3-benzyloxypropionate

HRID 613358Notes

Reaction equation

HRID 613358 reaction equation
[C:1](Cl)(=O)C(Cl)=O.[CH2:7]([O:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CN(C)[CH:22]=[O:23].[CH:25]1[CH:30]=[CH:29]C=CC=1>>[CH2:7]([O:14][CH2:15][CH2:16][C:17]([O:19][CH2:1][C:30]1([CH3:29])[CH2:22][O:23][CH2:25]1)=[O:18])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 4

HCID 241BenzeneHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 156088133-(Benzyloxy)propanoic acid

Product 1

HCID 541789563-Methyl-3-oxetanylmethyl 3-benzyloxypropionate

Procedure

Oxalyl chloride (880 mg) was added to a solution of 3-benzyloxypropionic acid (1.04 g) in benzen (10 ml). Subsequently, dimethylformamide (100 mg) was added. After the resultant mixture was stirred for 30 minutes at room temperature, benzen was distilled off. Azeotropic distillation was performed twice through use of benzen (10 ml), and the resultant residue was dissolved in tetrahydrofuran (10 ml). To the solution were added 3-methyl-3-oxetanyl-methyl alcohol (620 mg) and then triethylamine (620 mg). The mixture was stirred for 5 hours at room temperature. Ethyl acetate was added to the reaction mixture, followed by washing with sat. aq. K2CO3, water, 1N-HCl, water, and saturated brine and then drying over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate-hexane 2:1), to give 1.01 g of 3-methyl-3-oxetanylmethyl 3-benzyloxypropionate as a pale yellow oil.

Workup

  1. distillationbenzen was distilled off
  2. distillationAzeotropic distillation
  3. dissolutionthe resultant residue was dissolved in tetrahydrofuran (10 ml)
  4. additionTo the solution were added 3-methyl-3-oxetanyl-methyl alcohol (620 mg)
  5. additionEthyl acetate was added to the reaction mixture
  6. washby washing with sat. aq. K2CO3, water, 1N-HCl, water, and saturated brine
  7. dry with materialdrying over anhydrous magnesium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customthe residue was purified by silica gel column chromatography (ethyl acetate-hexane 2:1)

Sources & evidence

ORD record
ord-1fd6926837e84342af55af17129fd240
Source dataset
uspto-grants-1999_12
Patent number
US06008224

Reaction notes

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