1,3-Butadienyl acetate → HCID 18932672, compound

HRID 1452398Notes

Reaction equation

HRID 1452398 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9](=[O:12])[C:8]2[CH2:7][O:6][C:5]([C:17]([O:19][CH3:20])=[O:18])([C:13]([O:15][CH3:16])=[O:14])[CH2:4][C:3]1=2.C(O[CH:25]=[CH:26][CH:27]=[CH2:28])(=O)C>C1(C)C=CC=CC=1>[CH3:20][O:19][C:17]([C:5]1([C:13]([O:15][CH3:16])=[O:14])[O:6][CH2:7][C:8]2[C:9](=[O:12])[C:10]3[C:11]([C:2](=[O:1])[C:3]=2[CH2:4]1)=[CH:28][CH:27]=[CH:26][CH:25]=3)=[O:18]

Participants

4

Reactant 2

HCID 151951,3-Butadienyl acetateHCID 57279696HCID 57279696, compound

Product 1

HCID 18932672HCID 18932672, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 5,8-dioxo-3,3 bis (methoxycarbonyl)-5,8-dihydroisochroman (50 mg; 0.17 mmol) in toluene (4 ml) at room temperature was added 1-acetoxy-1,3 butadiene (113 μl; 1 mmol). The resulting mixture was stirred at room temperature for 24 hours. Air was then bubbled through for 30 minutes and the mixture was concentrated to a volume of ~1 ml and applied to silica gel column. Elution with 30% ethyl acetate in hexane afforded pure title compound (20 mg; 34%) as a yellow solid; m.p.: 210°-222° C. (dec):

Workup

  1. customAir was then bubbled through for 30 minutes
  2. concentrationthe mixture was concentrated to a volume of ~1 ml
  3. washElution with 30% ethyl acetate in hexane afforded pure title compound (20 mg; 34%) as a yellow solid

Sources & evidence

ORD record
ord-23a686a5040a4a3eafab3be8cc07600e
Source dataset
uspto-grants-1997_02
Patent number
US05606037

Reaction notes

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