Ethyl Acetate → HCID 19385655, compound

HRID 2399532Notes

Reaction equation

HRID 2399532 reaction equation
O[CH2:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:5]([CH2:24][CH2:25][CH3:26])[CH:4]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Br)(Br)(Br)[Br:47].CCOC(C)=O>C(Cl)Cl>[Br:47][CH2:2][C:3]1[CH:23]=[CH:22][C:6]([O:7][CH:8]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])=[C:5]([CH2:24][CH2:25][CH3:26])[CH:4]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11205Carbon tetrabromideHCID 11776TriphenylphosphineHCID 19385722HCID 19385722, compound

Product 1

HCID 19385655HCID 19385655, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 839 mg of the crude product from Step N in CH2Cl2 (20 mL) were added triphenylphosphine (525 mg, 2 mmol) and carbon tetrabromide (663 mg, 2 mmol) at 0° C. The solution was stirred at 0° C. for 1 hour and at rt for 15 hours. The solution was poured into EtOAc (100 mL). After the precipitate was removed, the filtrate was washed with H2O and brine, and dried over anhydrous MgSO4. Concentration afforded 302 mg of the title compound as a white solid.

Workup

  1. customAfter the precipitate was removed
  2. washthe filtrate was washed with H2O and brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationConcentration

Sources & evidence

ORD record
ord-376464512fac4917b84ee1bde42f30f2
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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