Methyl vinyl ketone → HCID 14257057, compound

HRID 622071Notes

Reaction equation

[Cl:1][C:2]1[C:7]2[C:8](=O)[CH:9]([CH2:11][CH2:12][CH3:13])[O:10][C:6]=2[CH:5]=[C:4]([O:15][CH3:16])[C:3]=1[Cl:17].N12[CH2:26][CH2:25][CH2:24][C:23]1=NCCC2.C(C(C)=[O:30])=C>O1CCCC1>[Cl:1][C:2]1[C:7]2[C:8]3=[CH:9][C:11](=[O:30])[CH2:12][CH2:13][C:26]3([CH2:25][CH2:24][CH3:23])[O:10][C:6]=2[CH:5]=[C:4]([O:15][CH3:16])[C:3]=1[Cl:17]

Participants

Conditions

Temperature: 25 °C

Procedure

A solution of 4,5-dichloro-6-methoxy-3-oxo-2-propylbenzofuran (0.785 g, 0.0029 mole) in tetrahydrofuran (THF) (8 ml) was warmed to 40° C. and treated with 1,5-diazabicyclo[4.3.0]non-5-ene (DBN) (10 μl) and then with methyl vinyl ketone (2 ml) over a 10 minute period. The reaction mixture was heated at 55° C. for 1/2 hour during which time DBN (2 x 10 μl) was added. The THF was evaporated in vacuo, the residual oil dissolved in ether and ethyl acetate, washed with water, dried over MgSO4 and evaporated in vacuo. The residual oil consisting of 4,5-dichloro-6-methoxy-3-oxo-2-(3-oxobutyl)-2-propylbenzofuran (0.81 g) was dissolved in ethanol (10 ml) and water (5 ml), treated with 5% NaOH (1 ml) and stirred at 25° C. for 72 hours. Treatment of the reaction mixture with water (5 ml) caused precipitation of 1,2-dichloro-3-methoxy-8-oxo-5a-propyl-5a,6,7,8,-tetrahydrodibenzofuran (0.6 g) which melted at 172°-173° C.

Workup

additionwas added
customThe THF was evaporated in vacuo
dissolutionthe residual oil dissolved in ether
washethyl acetate, washed with water
dry with materialdried over MgSO4
customevaporated in vacuo
dissolutionwas dissolved in ethanol (10 ml)
additionwater (5 ml), treated with 5% NaOH (1 ml)
customprecipitation of 1,2-dichloro-3-methoxy-8-oxo-5a-propyl-5a,6,7,8,-tetrahydrodibenzofuran (0.6 g) which melted at 172°-173° C.

Sources & evidence

ORD record: ord-1fee3ed714ec46338a67d9f543443425
Source dataset: uspto-grants-1988_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04769370

Reaction notes

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