Ethyl bromopyruvate → Ethyl 2-(diethoxymethyl)thiazole-4-carboxylate

Temperature

90 °C

To a solution of 2,2-bis(ethyloxy)ethanethioamide (648 mg) (available from Maybridge International) in ethanol (30 ml) was added ethyl bromopyruvate (0.598 ml) in ethanol (1 ml). Powdered molecular sieves (200 mg) were added and the mixture heated at 90° C. for 18 h. The mixture was filtered, washed with ethanol (10 ml) and the solvent removed in vacuo. The residue was triturated with DCM (15 ml) and the solid removed by filtration and washed with DCM (10 ml). The filtrate was concentrated in vacuo. Purification by chromatography on silica gel (70 g cartridge; FlashMaster II) eluting with 0-50% ethyl acetate in cyclohexane over 40 min gave the title compound (455 mg) as a yellow oil.

1. additionPowdered molecular sieves (200 mg) were added
2. filtrationThe mixture was filtered
3. washwashed with ethanol (10 ml)
4. customthe solvent removed in vacuo
5. customThe residue was triturated with DCM (15 ml)
6. customthe solid removed by filtration
7. washwashed with DCM (10 ml)
8. concentrationThe filtrate was concentrated in vacuo
9. customPurification by chromatography on silica gel (70 g cartridge; FlashMaster II)
10. washeluting with 0-50% ethyl acetate in cyclohexane over 40 min

ORD record

ord-f2cf7103058542448074cb347b4bec26

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658635B2