Sodium hydride → HCID 11206233, compound

HRID 352688Notes

Reaction equation

HRID 352688 reaction equation
OC(C)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])=[CH:7][N:6]=1.[H-].[Na+]>C1(C)C=CC=CC=1>[C:4]([C:5]1[CH:10]=[CH:9][C:8]([C@@H:11]2[CH2:15][CH2:14][CH2:13][N:12]2[CH3:16])=[CH:7][N:6]=1)#[CH:3]

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 11265060HCID 11265060, compound

Product 1

HCID 11206233HCID 11206233, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Compound 8 (0.12 g, 0.5 mmol) and NaH as a 60% dispersion in mineral oil (0.005 g, 0.13 mmol) were dissolved in dry toluene (10 mL). The stirred solution was slowly distilled until the boiling point of the distillate reached 110° C. The rest of the toluene was evaporated in vacuo. The residue was chromatographed [SiO2, CHCl3/MeOH, (10:1)] to give 0.062 g, (67%) of 9 as a yellow oil.

Workup

  1. distillationThe stirred solution was slowly distilled until the boiling point of the distillate
  2. customreached 110° C
  3. customThe rest of the toluene was evaporated in vacuo
  4. customThe residue was chromatographed [SiO2, CHCl3/MeOH, (10:1)]

Sources & evidence

ORD record
ord-2da0d3809c6a44008458ee6823952a4e
Source dataset
uspto-grants-2004_06
Patent number
US06747156B2

Reaction notes

Loading…