Ethanol → HCID 10660881, compound

HRID 1740888Notes

Reaction equation

HRID 1740888 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]O.[CH2:27]([OH:29])[CH3:28]>>[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]2[N:25]=[C:27]([CH3:28])[O:29][N:17]=2)[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 10680936HCID 10680936, compound

Product 1

HCID 10660881HCID 10660881, compoundYield 43%

Procedure

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

Sources & evidence

ORD record
ord-6a39789837e9463da56b6ecb68feba75
Source dataset
uspto-grants-1999_10
Patent number
US05972957

Reaction notes

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