1,2-Dichloroethane → HCID 20682829, compound

HRID 1595071Notes

Reaction equation

HRID 1595071 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 an hydrous 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. stirringwas stirred under ice-
  3. washwashed for separation with water
  4. dry with materialThe organic layer was dried over an hydrous 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-1a0ceed1ba6b469880251120c83c1d74
Source dataset
uspto-grants-2001_09
Patent number
US06284914B1

Reaction notes

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