Ethyl Acetate → 3-Ethyl-3,4-dihydro-1H-naphtho[2,3-c]pyran-5,10-dione

HRID 1452402Notes

Reaction equation

HRID 1452402 reaction equation
[O:1]=[C:2]1[CH:11]=[CH:10][C:9](=[O:12])[C:8]2[CH2:7][O:6][CH:5]([CH2:13][CH3:14])[CH2:4][C:3]1=2.C(O[CH:19]=[CH:20][CH:21]=[CH2:22])(=O)C.C(OCC)(=O)C>C1(C)C=CC=CC=1>[CH2:13]([CH:5]1[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:22][CH:21]=[CH:20][CH:19]=3)[CH3:14]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 151951,3-Butadienyl acetateHCID 18932707HCID 18932707, compound

Product 1

HCID 189326643-Ethyl-3,4-dihydro-1H-naphtho[2,3-c]pyran-5,10-dioneYield 20%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Following the procedure described in step 4, example 26, the starting quinone from step 3 herein (250 mg; 1.30 mmol) and 1-acetoxy-1,3-butadiene (876 μl; 7.8 mmol) were reacted in toluene (10 ml) to yield after chromatography using 2% ethyl acetate in toluene the title compound (62 mg; 20%) along with mixed fractions containing a lot of desired titled product (230 mg), M.P.: 98°-101° C.

Workup

  1. customto yield after chromatography

Sources & evidence

ORD record
ord-8039de40782f4463bacbf0afaeafa691
Source dataset
uspto-grants-1997_02
Patent number
US05606037

Reaction notes

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