1-Acetoxy-2-bromoethane → HCID 17937804, compound

HRID 1828651Notes

Reaction equation

HRID 1828651 reaction equation
[OH:1][C:2]1[CH:12]=[CH:11][C:5]2[O:6][CH:7]=[C:8]([O:9][CH3:10])[C:4]=2[CH:3]=1.[H-].[Na+].[C:15]([O:18][CH2:19][CH2:20]Br)(=[O:17])[CH3:16]>CN(C=O)C>[CH3:10][O:9][C:8]1[C:4]2[CH:3]=[C:2]([O:1][CH2:20][CH2:19][O:18][C:15](=[O:17])[CH3:16])[CH:12]=[CH:11][C:5]=2[O:6][CH:7]=1

Participants

5

Reactant 3

HCID 135641-Acetoxy-2-bromoethaneHCID 24758Sodium hydrideHCID 17937806HCID 17937806, compound

Product 1

HCID 17937804HCID 17937804, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

164 mg (1.0 mmol) XXI and 48 mg (1.2 mmol, 60%) NaH were stirred for 30 mins. in 20 ml DMF at 0° C. 227 μl (2.0 mmol, 97%) 2-bromoethyl acetate were added to the resulting suspension which was then stirred for 72 h at room temperature. The reaction was quenched by addition of 3 ml saturated NH4Cl solution and the solvents were removed in vacuo. The residue was taken up in ethyl acetate and water, the aqueous phase was extracted twice with ethyl acetate and the combined organic phases were dried over Na2SO4. After column filtration (40 g SiO2, n-hexane:ethyl acetate=2:1, applied with ethyl acetate), XXII was obtained in a yield of 220 mg (0.88 mmol, 88%).

Workup

  1. customat 0° C
  2. customThe reaction was quenched by addition of 3 ml saturated NH4Cl solution
  3. customthe solvents were removed in vacuo
  4. extractionwater, the aqueous phase was extracted twice with ethyl acetate
  5. dry with materialthe combined organic phases were dried over Na2SO4
  6. filtrationAfter column filtration (40 g SiO2, n-hexane:ethyl acetate=2:1, applied with ethyl acetate)

Sources & evidence

ORD record
ord-fb0d77d99f1e4f6ba95eee8a48229bf9
Source dataset
uspto-grants-2006_06
Patent number
US07060109B2

Reaction notes

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