1,2-Dichloroethane → HCID 20682829, compound

HRID 1857596Notes

Reaction equation

HRID 1857596 reaction equation
[Br:1][C@H:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([OH:5])=[O:4].[CH2:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(Cl)CCl>CN(C)C1C=CN=CC=1.C(Cl)Cl>[Br:1][C@H:2]([CH2:6][CH:7]([CH3:9])[CH3:8])[C:3]([O:5][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:4]

Participants

6

Reactant 3

HCID 111,2-DichloroethaneHCID 244Benzyl AlcoholHCID 12697060(2R)-2-bromo-4-methylpentanoic acid

Product 1

HCID 20682829HCID 20682829, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2(R)-Bromo-4-metylpentanoic acid (28.5 g, 146 mmol), benzyl alcohol (18.1 ml, 175 mmol) and 4-dimethylaminopyridine (1.90 g, 14.6 mmol) were dissolved in CH2Cl2 (140 ml), and added with EDC (35.6 g, 175 mmol) under ice-cooling and stirring. The mixture was stirred under ice-cooling for 1 hour and further at room temperature overnight and washed for separation with water, a saturated aqueous solution of NaHCO3 and then a saturated aqueous solution of NaCl two times respectively. The organic layer was dried over anhydrous MgSO4, evaporated under reduced pressure and purified by column chromatography (silica gel; 700 g, elution with the mixed solvent; n-hexane : AcOEt=40:1), giving the title compound (32.0 g, 77%) of a colorless oil.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred under ice-
  3. washwashed for separation with water
  4. dry with materialThe organic layer was dried over anhydrous MgSO4
  5. customevaporated under reduced pressure
  6. custompurified by column chromatography (silica gel
  7. wash700 g, elution with the mixed solvent

Sources & evidence

ORD record
ord-4fff15c540194f1180146199988ab2e7
Source dataset
uspto-grants-2000_11
Patent number
US06147114

Reaction notes

Loading…