1,3-Butadienyl acetate → HCID 57301325, compound

HRID 1598418Notes

Reaction equation

HRID 1598418 reaction equation
[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([C:12]([CH2:14][Br:15])=[O:13])[O:8][CH2:7][C:6]=2[C:5](=[O:16])[CH:4]=[CH:3]1.C(O[CH:21]=[CH:22][CH:23]=[CH2:24])(=O)C>C1(C)C=CC=CC=1>[O:1]=[C:2]1[C:11]2[CH:10]=[C:9]([C:12]([CH2:14][Br:15])=[O:13])[O:8][CH2:7][C:6]=2[C:5](=[O:16])[C:4]2[C:3]1=[CH:21][CH:22]=[CH:23][CH:24]=2

Participants

4

Reactant 2

HCID 151951,3-Butadienyl acetateHCID 131720592HCID 131720592, compound

Product 1

HCID 57301325HCID 57301325, compoundYield 62%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution containing one equivalent of isochromandione (263 mg, 0.92 mmol) from step 1 (example 6) in 25 ml of dry toluene was added three equivalents (2.7 mmol) of acetoxybutadiene. The reaction mixture was stirred overnight under argon at room temperature and then two hours at 60° C. After removal of solvent, the crude product was flash chromatographed (toluene/EtOAc,9:1). The titled orange compound was isolated (192 mg) in 62% yield.

Workup

  1. customtwo hours
  2. customat 60° C
  3. customAfter removal of solvent
  4. customchromatographed (toluene/EtOAc,9:1)
  5. customThe titled orange compound was isolated (192 mg) in 62% yield

Sources & evidence

ORD record
ord-5f46d0a482c84ce5bbdb3ce3fac68538
Source dataset
uspto-grants-1998_04
Patent number
US05736523

Reaction notes

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