Sodium Hydroxide → HCID 14117126, compound

HRID 1193979Notes

Reaction equation

HRID 1193979 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][N:5]=[CH:4][CH:3]=1.[OH-].[CH2:9]([N+](C)(C)C)[C:10]1[CH:15]=CC=[CH:12][CH:11]=1.CC(Cl)(C)C#C.[OH-].[Na+]>CO.C(Cl)Cl.O>[CH3:9][C:10]1([CH3:15])[O:1][C:2]2[CH:7]=[CH:6][N:5]=[CH:4][C:3]=2[CH:12]=[CH:11]1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 66854Benzyltrimethylammonium hydroxideHCID 706791-Butyne, 3-chloro-3-methyl-HCID 178418642HCID 178418642, compound

Product 1

HCID 14117126HCID 14117126, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

p-Hydroxypyridine (32.0 g), 40% benzyltrimethylammonium hydroxide in MeOH (50.7 g) and 3-methyl-3-chlorobut-1-yne (37.4 g) were dissolved in CH2Cl2 (150 mL). To this stirred solution was added NaOH pellets (14.5 g) dissolved in H2O (150 mL) and the resulting mixture stirred vigorously at room temperature for 3.75 days. The layers were separated and the aqueous layer further extracted with CHCl3. The combined organic layers were evaporated and the resulting brown oil was taken up in Et2O and washed with 10% NaOH solution, H20 and brine before drying over anh. MgSO4. Filtration and evaporation yielded an orange oil (21.0 g) which was boiled in o-dichlorobenzene under N2 for 1 h. Evaporation of the solvent and distillation gave the title pyranopyridine (9.2 g): bp 110° C. /0.18 mmHg; NMR (CDCl3) δ 1.47 (s, 6H)

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer further extracted with CHCl3
  3. customThe combined organic layers were evaporated
  4. washwashed with 10% NaOH solution, H20 and brine
  5. dry with materialbefore drying over anh. MgSO4
  6. filtrationFiltration and evaporation

Sources & evidence

ORD record
ord-5b0ffdbcf4e94df1bb1aee5589b79f9a
Source dataset
uspto-grants-1989_03
Patent number
US04812459

Reaction notes

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