Benzyl Bromide → HCID 22870962, compound

HRID 1108325Notes

Reaction equation

HRID 1108325 reaction equation
[CH:1]1([CH2:4][C@@H:5]([OH:9])[C:6]([OH:8])=[O:7])[CH2:3][CH2:2]1.C(N(CC)CC)C.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(OCC)(=O)C>[CH:1]1([CH2:4][C@@H:5]([OH:9])[C:6]([O:8][CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:7])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 8471TriethylamineHCID 22870961(2R)-3-Cyclopropyl-2-hydroxypropanoic acid

Product 1

HCID 22870962HCID 22870962, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3.95 g of 3-cyclopropyl-2(R)-hydroxypropionic acid in 50 ml of ethyl acetate was treated with 5.32 ml of triethylamine and 3.8 ml of benzyl bromide. The mixture was stirred and heated under reflux for 3 hours, then allowed to cool to room temperature overnight. The suspension was washed with 2M hydrochloric acid, water and saturated sodium chloride solution. After drying over anhydrous magnesium sulphate the solvent was evaporated. The residue was purified by flash chromatography on silica gel using hexane/ethyl acetate (2:1) for the elution to give 3.36 g of benzyl 3-cyclopropyl-2(R)-hydroxypropionate in the form of a yellow oil.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 3 hours
  3. washThe suspension was washed with 2M hydrochloric acid, water and saturated sodium chloride solution
  4. dry with materialAfter drying over anhydrous magnesium sulphate the solvent
  5. customwas evaporated
  6. customThe residue was purified by flash chromatography on silica gel
  7. washfor the elution

Sources & evidence

ORD record
ord-24f4afcff53c466f83266adaf0025bd2
Source dataset
uspto-grants-2000_05
Patent number
US06066662

Reaction notes

Loading…