Ethyl Acetate → HCID 19385655, compound

HRID 2255642Notes

Reaction equation

HRID 2255642 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-b7a0f6d5ed374c7bac8e79bfda088f46
Source dataset
uspto-grants-1993_08
Patent number
US05240938

Reaction notes

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