Allyl bromide → Trans-2-(4-allyloxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxyphenyl)-1,3-dithiolane

HRID 260976Notes

Reaction equation

[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C@H:11]2[S:15][C@H:14]([C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)[CH2:13][S:12]2)=[CH:4][C:3]=1[O:28][CH3:29].[CH2:30](Br)[CH:31]=[CH2:32].C1OCCOCCOCCOCCOCCOC1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:32]([O:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C@H:11]2[S:15][C@H:14]([C:16]3[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=3)[CH2:13][S:12]2)=[CH:4][C:3]=1[O:28][CH3:29])[CH:31]=[CH2:30]

Participants

Conditions

Temperature: 50 °C

Procedure

Trans-2-(4-hydroxy-3-methoxy-5-nitrophenyl)-4-(3,4,5-trimethoxy-phenyl)-1,3-dithiolane (21) (2.50 g, 5.69 mmole) was dissolved in 30 ml dry DMF and allyl bromide (0.963 g, 7.97 mmole) was added by syringe. To this solution was added 100 mg of 18-crown-6 and potassium carbonate (0.785 g, 5.69 mmole). The reaction was stirred at 50° C. under an argon atmosphere for 4 hours. The reaction was quenched with 10% HCl and extracted with diethyl ether. The organic layer was dried over MgSO4, and concentrated to a yellow oil in vacuo which was purified by flash column chromatography with 3:1-2:1 hexane/ethyl acetate as eluent. (2.60 g, 95% yield: colorless oil).

Workup

customThe reaction was quenched with 10% HCl
extractionextracted with diethyl ether
dry with materialThe organic layer was dried over MgSO4
concentrationconcentrated to a yellow oil in vacuo which
customwas purified by flash column chromatography with 3:1-2:1 hexane/ethyl acetate as eluent

Sources & evidence

ORD record: ord-a6cf6e13e1124eca8c395670b9ca4b37
Source dataset: uspto-grants-1996_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05530141

Reaction notes

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