Potassium Hydroxide → HCID 12138719, compound

HRID 2308381Notes

Reaction equation

HRID 2308381 reaction equation
[OH-].[K+].[O:3]1[C:8]2[CH:9]=[CH:10][C:11]([CH:13]=[O:14])=[CH:12][C:7]=2[O:6][CH2:5][CH2:4]1.[N+:15]([CH2:17][C:18]([N:20]1[CH2:24][CH2:23][CH2:22][CH2:21]1)=[O:19])#[C-:16]>CO>[O:3]1[C:8]2[CH:9]=[CH:10][C:11]([C@@H:13]3[O:14][CH:16]=[N:15][C@H:17]3[C:18]([N:20]3[CH2:24][CH2:23][CH2:22][CH2:21]3)=[O:19])=[CH:12][C:7]=2[O:6][CH2:5][CH2:4]1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 2481272,3-Dihydro-1,4-benzodioxin-6-carbaldehydeHCID 6455476Pyrrolidine, 1-(isocyanoacetyl)-

Product 1

HCID 12138719HCID 12138719, compoundYield 68.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred and cooled (0° C.) solution of potassium hydroxide (2.70 g, 48.1 mmol) in methanol (30 ml) was added a mixture of 1,4-benzodioxan-6-carboxaldehyde (8.20 g, 50.0 mmol) and the product from Example 1 (6.30 g, 45.6 mmol). The solution was stirred overnight 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 (magnesium sulfate). Concentration afforded crude product as a golden, glassy solid. Flash chromatography over silica (ethyl acetate) yielded 9.40 g (68%) of product as a colorless glassy solid. 1H NMR (CDCl3) δ 6.99 (s, 1H), 6.90-6.78 (m, 3H), 6.00 (d, J=7.3, 1H), 4.58, (d, J=7.3, 1H), 4.26 (s, 4H), 3.95-3.87 (m, 1H), 3.55-3.41 (m, 3H), 2.04-1.80 (m, 4H) ppm.

Workup

  1. additionwas added
  2. stirringThe solution was stirred overnight
  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 (magnesium sulfate)
  8. concentrationConcentration
  9. customafforded crude product as a golden, glassy solid

Sources & evidence

ORD record
ord-48b3cbdbad024d448f1fb752b3710a84
Source dataset
uspto-grants-2004_12
Patent number
US06835831B2

Reaction notes

Loading…