Dimethylformamide → HCID 66597223, compound

HRID 1627762Notes

Reaction equation

[NH2:1][C:2]1[S:10][C:5]2[CH2:6][O:7][CH2:8][CH2:9][C:4]=2[C:3]=1[C:11]([C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1)=O.Cl[Si](C)(C)C.CN([CH:28]=[O:29])C>>[CH3:2][C:3]1[C:4]([CH2:5][C:6]([O:29][CH3:28])=[O:7])=[C:11]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[C:3]2[C:4]3[CH2:9][CH2:8][O:7][CH2:6][C:5]=3[S:10][C:2]=2[N:1]=1

Participants

Reactant 3

HCID 6228Dimethylformamide

HCID 6397Chlorotrimethylsilane

HCID 210370771256257-07-4

Product 1

HCID 66597223HCID 66597223, compoundYield 36%

Procedure

This compound was prepared according to the procedure B from (2-amino-4,7-dihydro-5H-thieno[2,3-c]pyran-3-yl)-(p-tolyl)-methanone (0.546 g; 2 mmol), methyl levunilate (0.282 mL; 2.2 mmol), chlorotrimethylsilane (1 mL; 8 mmol) in DMF (8 mL) for 22 h. Purification by flash chromatography on silica gel using a gradient of ethyl acetate (2-80%) in heptane furnished 0.270 g (36%) of the title compound as a yellow solid.

Workup

customThis compound was prepared
customPurification by flash chromatography on silica gel using a gradient of ethyl acetate (2-80%) in heptane

Sources & evidence

ORD record: ord-3329e816dd2f4443a26066d501eabf2e
Source dataset: uspto-grants-2014_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08785638B2

Reaction notes

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