1-Decanol → HCID 10356104, compound

HRID 382227Notes

Reaction equation

HRID 382227 reaction equation
[CH2:1]([OH:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[H-].[Na+].Cl[C:15]1[N:23]=[CH:22][N:21]=[C:20]2[C:16]=1[NH:17][CH:18]=[N:19]2>O1CCCC1>[CH2:1]([O:11][C:15]1[N:23]=[CH:22][N:21]=[C:20]2[C:16]=1[NH:17][CH:18]=[N:19]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 81741-DecanolHCID 24758Sodium hydrideHCID 53592776-Chloropurine

Product 1

HCID 10356104HCID 10356104, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Decanol (13ml, 68.2mmol) was added in one portion to a stirred suspension of a 60% dispersion of sodium hydride in oil (2.70 g, 67.5mmol) in dry tetrahydrofuran (70 ml) under an atmosphere of nitrogen. Gas was evolved. After 0.5 h 6-chloropurine (3.00 g, 19.4 mmol) was added and the suspension heated at reflux for 3.5 h. The tetrahydrofuran was removed in vacuo and the residue suspended in dilute hydrochloric acid (200 ml). The acidic suspension was stirred for 1 h then neutralised with saturated sodium hydrogen carbonate solution. The suspension was stirred vigorously with 60-80 petroleum ether (500 ml) and the solid removed by filtration. The solid was recrystallised from methanol to give a white solid (3.29 g, 11.9 mmol, 61%).

Workup

  1. temperaturethe suspension heated
  2. temperatureat reflux for 3.5 h
  3. customThe tetrahydrofuran was removed in vacuo
  4. stirringThe suspension was stirred vigorously with 60-80 petroleum ether (500 ml)
  5. customthe solid removed by filtration
  6. customThe solid was recrystallised from methanol

Sources & evidence

ORD record
ord-6937d6ebafde4a0393d0ca0ef60b5956
Source dataset
uspto-grants-2001_10
Patent number
US06309811B2

Reaction notes

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