Potassium Carbonate → HCID 86751350, compound

HRID 399499Notes

Reaction equation

HRID 399499 reaction equation
[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([C:16]#[N:17])[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:25][OH:26]>C(O)C>[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([C:16](=[N:25][OH:26])[NH2:17])[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 10680936HCID 10680936, compound

Product 1

HCID 86751350HCID 86751350, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 7-tert-butyl-5-cyano-2,3-dihydro-3,3-dimethylbenzo[b]furan (6.39 g, 27.9 mmol), potassium carbonate (15.80 g, 114.0 mmol), hydroxylamine hydrochloride (7.93 g, 114.0 mmol), and 135 mL of ethanol is heated at reflux for 20 h. The reaction mixture is cooled to room temperature, filtered, and concentrated in vacuo to give a solid residue. Purification by flash column chromatography on silica gel (20% ethyl acetate-hexane→5% methanol-dichloromethane) furnishes about 3.13 g (43%) of the title compound as a colorless foamy solid: mp 109°-110 ° C.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 20 h
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a solid residue
  6. customPurification by flash column chromatography on silica gel (20% ethyl acetate-hexane→5% methanol-dichloromethane)

Sources & evidence

ORD record
ord-94b2ead83c62405aa617dcb000dd8a7a
Source dataset
uspto-grants-1998_10
Patent number
US05821250

Reaction notes

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