1-Bromopropane → HCID 86736723, compound

HRID 1447664Notes

Reaction equation

HRID 1447664 reaction equation
[CH2:1]([O:8][C@@H:9]1[C@@H:14]([OH:15])[C@H:13]2[CH2:16][O:17][C@H:11]([O:12]2)[C@@H:10]1[O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[K+].[CH2:27](Br)[CH2:28][CH3:29]>CS(C)=O>[CH2:1]([O:8][C@@H:9]1[C@@H:14]([O:15][CH2:27][CH2:28][CH3:29])[C@H:13]2[CH2:16][O:17][C@H:11]([O:12]2)[C@@H:10]1[O:18][CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][O:20]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 78401-Bromopropane2×HCID 14797Potassium Hydroxide2×HCID 86736724HCID 86736724, compound

Product 1

HCID 86736723HCID 86736723, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Conditions

Temperature
50 °C

Procedure

A solution of 10 g of 1,6-anhydro-3-O-benzyl-2-O-tetrahydropyranyl-β-D-gulopyranose in 20 ml of absolute dimethylsulphoxide is treated with 3 g of potassium hydroxide powder, while stirring and with the exclusion of moisture, in a nitrogen atmosphere, and the mixture is warmed to 50° C. A solution of 3 ml of propyl bromide in 10 ml of dimethylsulphoxide is added dropwise at this temperature in the course of 2 hours and the reaction mixture is stirred for a further 3 hours. A further 3 g of potassium hydroxide powder are added, a solution of 3 ml of propyl bromide in 10 ml of dimethylsulphoxide is added dropwise and the mixture is stirred for 2 hours. The reaction mixture is now cooled and poured into ice-water. The resulting mixture is extracted with ether and the ether phase is washed with water until neutral and dried over magnesium sulphate. After evaporating off the solvent, 1,6-anhydro-3-O-benzyl-4-O-propyl-2-O-tetrahydropyranyl-β-D-gulopyranose is obtained in the form of yellow oil with a Rf value of 0.42 on silica gel thin layer plates in the system methylene chloride/ethyl acetate, 85:15.

Workup

  1. stirringthe reaction mixture is stirred for a further 3 hours
  2. stirringthe mixture is stirred for 2 hours
  3. temperatureThe reaction mixture is now cooled
  4. extractionThe resulting mixture is extracted with ether
  5. washthe ether phase is washed with water until neutral and
  6. dry with materialdried over magnesium sulphate
  7. customAfter evaporating off the solvent

Sources & evidence

ORD record
ord-5b9e8122c4844d489d5d60e2b9275fd2
Source dataset
uspto-grants-1979_12
Patent number
US04177344

Reaction notes

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