1,3-Butadienyl acetate → HCID 22870049, compound

HRID 1598426Notes

Reaction equation

HRID 1598426 reaction equation
[C:1]([NH:4][C@H:5]1[C:14]2[C:13](=[O:15])[CH:12]=[CH:11][C:10](=[O:16])[C:9]=2[CH2:8][C@H:7]([CH2:17][CH3:18])[O:6]1)(=[O:3])[CH3:2].C(O[CH:23]=[CH:24][CH:25]=[CH2:26])(=O)C>C1(C)C=CC=CC=1>[O:16]=[C:10]1[C:9]2[CH2:8][C@H:7]([CH2:17][CH3:18])[O:6][C@@H:5]([NH:4][C:1](=[O:3])[CH3:2])[C:14]=2[C:13](=[O:15])[C:12]2[C:11]1=[CH:23][CH:24]=[CH:25][CH:26]=2

Participants

4

Reactant 2

HCID 151951,3-Butadienyl acetateHCID 67615717HCID 67615717, compound

Product 1

HCID 22870049HCID 22870049, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of the starting quinone from step 1 herein (56 mg; 0.22 mmol) in toluene (50 ml) was added 1-acetoxy-1,3-butadiene (30 μl; 11 eq). The mixture was stirred overnight at room temperature and was then concentrated and applied to a column of silica gel using 1-15% acetone in benzene to elute the product which was then recrystallized from dichloromethane:pentane affording the title compound as a yellow solid (10 mg; 15%).

Workup

  1. concentrationwas then concentrated
  2. washto elute the product which
  3. customwas then recrystallized from dichloromethane

Sources & evidence

ORD record
ord-79d08a52d9ff4f13b5c48e785747d87a
Source dataset
uspto-grants-1998_04
Patent number
US05736523

Reaction notes

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