Sodium hydride → HCID 20481334, compound

HRID 1648940Notes

Reaction equation

HRID 1648940 reaction equation
[C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])(=[O:4])[CH2:2][OH:3].[H-].[Na+].[Cl:12][C:13]1[CH:29]=[CH:28][CH:27]=[CH:26][C:14]=1[CH2:15][N:16]1[CH2:22][CH2:21][C:20]([CH:23]=O)=[C:19](Cl)[CH2:18][CH2:17]1>O1CCOCC1>[Cl:12][C:13]1[CH:29]=[CH:28][CH:27]=[CH:26][C:14]=1[CH2:15][N:16]1[CH2:22][CH2:21][C:20]2[CH:23]=[C:2]([C:1]([O:5][CH2:6][CH2:7][CH2:8][CH3:9])=[O:4])[O:3][C:19]=2[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81882Butyl GlycolateHCID 20481346HCID 20481346, compound

Product 1

HCID 20481334HCID 20481334, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

2.0 gm (0.015 mol) of butyl glycolate were slowly added dropwise, while vigorously stirring, to a suspension of 0.72 gm (0.015 mol) of 50% sodium hydride in 10 ml of absolute dioxane at room temperature while dry nitrogen was introduced. The temperature of the intensely foaming reaction mixture was kept below 30° C. by cooling with ice-cold water, as needed. After 11/2 hours of stirring at room temperature, a solution of 2.84 gm (0.010 mol) of 1-(2-chlorobenzyl)-4-chloro-5-formyl-2,3,6,7-tetrahydro-1H-azepine in 20 ml of absolute dioxane was added dropwise, whereupon the temperature of the reaction mixture rose from 20° C. to about 33° C. Then, the mixture was stirred for two hours at room temperature, poured into about 150 ml of ice-cold water, and the aqueous mixture was extracted three times with ethyl acetate. The combined organic phases were extracted with water three times, dried over sodium sulfate and concentrated by evaporation. The residue was purified by column chromatography on silicagel, using chloroform/ethyl acetate (93:7) as eluant.

Workup

  1. additionwas introduced
  2. customreaction mixture
  3. customwas kept below 30° C.
  4. temperatureby cooling with ice-cold water
  5. customrose from 20° C. to about 33° C
  6. stirringThen, the mixture was stirred for two hours at room temperature
  7. extractionthe aqueous mixture was extracted three times with ethyl acetate
  8. extractionThe combined organic phases were extracted with water three times
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated by evaporation
  11. customThe residue was purified by column chromatography on silicagel

Sources & evidence

ORD record
ord-257fd43e27d14c5a8b507bf3f2a0fc1a
Source dataset
uspto-grants-1983_11
Patent number
US04414225

Reaction notes

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