Triethylamine → methyl 5,6-dihydro-4H-cyclopenta[b]thiophene-2-carboxylate

To a 100-mL round-bottom flask containing a solution of 2-chlorocyclopent-1-ene-1-carbaldehyde (1.2 g, 9.19 mmol, 1.00 equiv) and methyl 2-sulfanylacetate (1.17 g, 11.02 mmol, 1.20 equiv) in pyridine (10 mL) was added triethylamine (2 mL) dropwise at 0° C. The resulting solution was stirred for 1 h at room temperature. The reaction was then quenched by the addition of 2 mL of 48% aqueous KOH solution and diluted with 100 mL of water. The resulting solution was extracted with 3×100 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum to give 1.3 g (78%) of methyl 4H,5H,6H-cyclopenta[b]thiophene-2-carboxylate as a yellow solid. MS (ES): m/z 183 (M+H)+.

1. customThe reaction was then quenched by the addition of 2 mL of 48% aqueous KOH solution
2. additiondiluted with 100 mL of water
3. extractionThe resulting solution was extracted with 3×100 mL of ethyl acetate
4. washThe combined organic layers were washed with brine
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationconcentrated under vacuum

ORD record

ord-701e644af19b4261b493d35d201b75e1

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067948B2