Water → 2-(2-Benzyloxy-6-methoxy-phenyl)-5,5-dimethyl-oxazolidin-4-one

HRID 2191606Notes

Reaction equation

HRID 2191606 reaction equation
[OH:1][C:2]([CH3:7])([CH3:6])[C:3]([NH2:5])=[O:4].[CH2:8]([O:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:17]=1[CH:18]=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>CCCCCCC>[CH2:8]([O:15][C:16]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:17]=1[CH:18]1[NH:5][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[O:1]1)[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 962WaterHCID 83059Propanamide, 2-hydroxy-2-methyl-HCID 37354792-(Benzyloxy)-6-methoxybenzaldehyde

Product 1

HCID 667893212-(2-Benzyloxy-6-methoxy-phenyl)-5,5-dimethyl-oxazolidin-4-oneYield 61%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
240 °C

Procedure

A mixture of commercially available 2-hydroxyisobutyramide (638.5 mg, 3 eq), 2-benzyloxy-6-methoxy-benzaldehyde (500 mg) (Katritzky A. R. et al ARKIVOC 2001, 2, 3, 3-12) is heated at 240° C. for 5 min using microwave irradiation (Lecolier S. et al Chimica Therapeutica 1969, 4,6, 437-445). The crude oil is poured into water and extracted with DCM. The combined organic extracts are dried (MgSO4), filtered and concentrated to yield a crude oil. FC (EN n-heptane: 1/1 to 1/0) gives the title compound as a yellow solid (0.41 g, 61%); LC-MS: tR=0.65 min; [M+H]+=328.22.

Workup

  1. custommicrowave irradiation (Lecolier S. et al Chimica Therapeutica 1969, 4,6, 437-445)
  2. extractionextracted with DCM
  3. dry with materialThe combined organic extracts are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto yield a crude oil

Sources & evidence

ORD record
ord-982df8d48a9c49419754f9e376e5ac33
Source dataset
uspto-grants-2012_12
Patent number
US08329706B2

Reaction notes

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