Water → HCID 86746501, compound

HRID 1646688Notes

Reaction equation

[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH:6]([C:13]1[S:14][CH:15]=[CH:16][CH:17]=1)[C:7]1[N:11]([CH3:12])[CH:10]=[N:9][CH:8]=1.[Li][CH2:19]CCC.[C:23]1(=[O:28])[O:27][CH2:26][CH:25]=C1.O>O1CCCC1.CCCCCC.C(=O)=O>[CH3:19][N:9]1[C:8]([C:7]2([CH:6]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[C:2]3[S:1][CH:5]=[CH:4][CH:3]=3)[CH2:25][CH2:26][O:27][C:23]2=[O:28])=[CH:12][N:11]=[CH:10]1

Participants

Conditions

Temperature: -78 °C

Procedure

16.4 g (52.5 mmol) of 5-dithiophenylmethyl-1-methylimidazole are dissolved in 240 ml of tetrahydrofuran and cooled to -78° C. 52.5 mmol of n-BuLi in 32 ml of hexane are added dropwise to this. After 30 minutes at -78° C., 4.9 ml (69.8 mmol) of γ-crotonolactone are added and, after a further 1.5 hours, 250 ml of water are added dropwise while cooling in dry ice, and the mixture is allowed to warm to room temperature. It is then washed with ethyl acetate, acidified with glacial acetic acid and again extracted with ethyl acetate. The organic phase is dried over magnesium sulfate and concentrated in vacuo. The residue obtained in this way (13.8 g) is chromatographed on silica gel with dichloromethane/methanol (9:1). 6.6 g (16.6 mmol, 32%) of 3-(1-methylimidazol-5-yl-(dithiophenyl)methylbutyrolactone are obtained as a white powder of melting point 80° C.

Workup

temperatureto warm to room temperature
washIt is then washed with ethyl acetate
extractionagain extracted with ethyl acetate
dry with materialThe organic phase is dried over magnesium sulfate
concentrationconcentrated in vacuo
customThe residue obtained in this way (13.8 g)
customis chromatographed on silica gel with dichloromethane/methanol (9:1)

Sources & evidence

ORD record: ord-b0845dae43ae4c2597dd179d44fe1951
Source dataset: uspto-grants-1993_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05180837

Reaction notes

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