Potassium Hydroxide → HCID 66646062, compound

HRID 1971260Notes

Reaction equation

HRID 1971260 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([CH:9]=[O:10])=[CH:7][CH:6]=1.[N+:13]([CH2:15][C:16]([N:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)=[O:17])#[C-:14]>CO>[CH3:3][O:4][C:5]1[CH:12]=[CH:11][C:8]([C@@H:9]2[O:10][CH:14]=[N:13][C@H:15]2[C:16]([N:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)=[O:17])=[CH:7][CH:6]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 312444-MethoxybenzaldehydeHCID 6455476Pyrrolidine, 1-(isocyanoacetyl)-

Product 1

HCID 66646062HCID 66646062, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred and cooled (0° C.) solution of potassium hydroxide (0.37 g, 6.57 mmol) in methanol (30 mL) was added a mixture of 4-methoxy-benzaldehyde (0.88 mL, 7.23 mmol) and 2-isocyano-1-(pyrrolidin-1-yl)ethanone BLE 04098 (1.0 g, 6.57 mmol). The solution was stirred 4 h with continued cooling and then concentrated. The residue was partitioned between ethyl acetate and water. The organic layer was combined with additional ethyl acetate extracts, washed with aqueous sodium chloride and dried over MgSO4. Concentration afforded a crude product as a glassy solid. Flash chromatography over silica (ethyl acetate) yielded to trans-(4,5-dihydro-5-(4-methoxyphenyl)oxazol-4-yl)(pyrrolidin-1-yl)methanone SLA 07074 as a pale yellow solid (1.2 g, 90.5%).

Workup

  1. additionwas added
  2. stirringThe solution was stirred 4 h
  3. temperaturewith continued cooling
  4. concentrationconcentrated
  5. customThe residue was partitioned between ethyl acetate and water
  6. washwashed with aqueous sodium chloride
  7. dry with materialdried over MgSO4
  8. concentrationConcentration
  9. customafforded a crude product as a glassy solid

Sources & evidence

ORD record
ord-e064f104a05e4865bb7c4cd873f4d8ce
Source dataset
uspto-grants-2013_04
Patent number
US08431599B2

Reaction notes

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