Sodium hydride → HCID 21450346, compound

HRID 596591Notes

Reaction equation

HRID 596591 reaction equation
[OH:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12]2[O:13][C:14]3[C:15]([N:20]=2)=[N:16][CH:17]=[CH:18][CH:19]=3)[CH:3]=1.[H-].[Na+].[CH2:23](I)[CH2:24][CH3:25]>CN(C)C=O>[CH2:23]([O:1][C:2]1[C:11]2[CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[CH:5]=[C:4]([C:12]2[O:13][C:14]3[C:15]([N:20]=2)=[N:16][CH:17]=[CH:18][CH:19]=3)[CH:3]=1)[CH2:24][CH3:25]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 21450340HCID 21450340, compound

Product 1

HCID 21450346HCID 21450346, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 5.0 mmoles of product from Step D in 5 ml. of dimethylformamide is treated with 5.0 mmoles of sodium hydride/mineral oil emulsion. After stirring 10 minutes 1.0 g. of propyl iodide is added. After stirring 2 hours, the mixture is concentrated in vacuo to remove the dimethylformamide. Water (10 ml.) is added to the residue and the solids are collected and recrystallized from cyclohexane to give 2-(4-propoxy-5,6,7,8-tetrahydronaphth-2-yl)oxazolo[4,5-b]pyridine.

Workup

  1. stirringAfter stirring 2 hours
  2. concentrationthe mixture is concentrated in vacuo
  3. customto remove the dimethylformamide
  4. additionWater (10 ml.) is added to the residue
  5. customthe solids are collected
  6. customrecrystallized from cyclohexane

Sources & evidence

ORD record
ord-62ea3c53aa16460ba93611464f099dd6
Source dataset
uspto-grants-1977_03
Patent number
US04011326

Reaction notes

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