Dimethylformamide → 5-(Benzyloxy)pentan-1-ol

HRID 1838897Notes

Reaction equation

HRID 1838897 reaction equation
[H-].[Na+].CN(C=O)C.[CH2:8]([OH:14])[CH2:9][CH2:10][CH2:11][CH2:12][OH:13].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O>[CH2:15]([O:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][OH:14])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 4

HCID 6228Dimethylformamide3×HCID 7498Benzyl BromideHCID 81051,5-PentanediolHCID 24758Sodium hydride

Product 1

HCID 2211945-(Benzyloxy)pentan-1-ol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
-20 °C

Procedure

31.5 g of sodium hydride (60% strength) are ire educed into 900 ml of abs. DMF in portions at room temperature. 104.8 ml of 1,5-pentanediol in 450 ml of abs. DMF are added dropwise to the suspension cooled to −20° C., such that the internal temperature does not exceed −15° C. After addition is complete, a solution of 121 ml of benzyl bromide in 870 ml of abs. DMF is rapidly added dropwise and the reaction mixture is then stirred at room temperature for 30 minutes. The reaction is ended by careful addition of 315 ml of water. For work-up, the reaction mixture is stirred into 1.5 l of water and extracted 3 times with 1 l of ether in each case. The ethereal phases are combined, washed with water, dried over magnesium sulphate and concentrated in vacuo. Chromatography on silica gel using a hexane-ethyl acetate gradient yields 85 g of 5-benzyloxypentan-1-ol as an oil.

Workup

  1. customat room temperature
  2. customdoes not exceed −15° C
  3. additionAfter addition
  4. extractionextracted 3 times with 1 l of ether in each case
  5. washwashed with water
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b7f722286cfa42809c17ee99a8be2adb
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

Loading…