Isopropanol → HCID 54244612, compound

HRID 1505225Notes

Reaction equation

HRID 1505225 reaction equation
F[C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[H-].[Na+].[CH:13]([OH:16])([CH3:15])[CH3:14]>>[CH:13]([O:16][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5])([CH3:15])[CH3:14]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24758Sodium hydrideHCID 27784432-Fluoro-4-methylbenzonitrile

Product 1

HCID 54244612HCID 54244612, compound

Conditions

Temperature
50 °C

Procedure

The 2-fluoro-4-methyl-benzonitrile (0.8 g, 3.99 mmol) was added in small portion to a mixture of NaH 60% (4 mol eq, 0.61 g) in isopropanol (30 mL). The reaction mixture was heated at 50° C. overnight. The solvent was distilled and water was added to the residue. The aqueous solution was extracted with EtOAc (3×25 mL) and the organic phases were evaporated at reduced pressure to give 30a as a deliquescent white solid (1.09 g, 6.22 mmol). 1HNMR (DMSO, 200 MHz) δ 1.21 (s, 3H), 1.28 (s, 3H), 2.10 (s, 3H), 4.89 (m, 1H), 7.41 (d, 1H), 7.55 (s, 1H), 7.89 (m, 1H).

Workup

  1. distillationThe solvent was distilled
  2. additionwater was added to the residue
  3. extractionThe aqueous solution was extracted with EtOAc (3×25 mL)
  4. customthe organic phases were evaporated at reduced pressure

Sources & evidence

ORD record
ord-f66bd9c629b14c8c9c3e139febc2f9dc
Source dataset
uspto-grants-2015_12
Patent number
US09216975B2

Reaction notes

Loading…