Triethylamine → Methyl 4,5,6,7-tetrahydro-1-benzothiophene-2-carboxylate

To a solution of 2-chlorocyclohex-1-enecarbaldehyde (50 g, 346 mmol) and methyl-2-mercaptoacetate (40 g, 380 mmol) in Pyridine (100 mL) was added triethylamine (105 g, 1037 mmol) at room temperature. The mixture was stirred for 2 h, and partitioned between ethyl acetate (200 mL) and 1N aqueous HCl (50 mL). The separated organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness, which was dissolved in Methanol (100 mL). To the above solution was added sodium methoxide (1.9 g, 34.6 mmol), then, the mixture was heated at reflux for 3 hrs, which was poured into ice water and partitioned between ethyl acetate (200 mL) and 1N aqueous NaHCO3 (50 mL). The separated organic layer was washed with brine, dried over Na2SO4 and evaporated to dryness, which was purified by silica gel chromatography eluted with PE:ethyl acetate 10:1 to give title product (25 g, 36% yield) as yellow solid. LCMS (m/z) ES+=197 (M+1)

1. custompartitioned between ethyl acetate (200 mL) and 1N aqueous HCl (50 mL)
2. washThe separated organic layer was washed with brine
3. dry with materialdried over Na2SO4
4. customevaporated to dryness, which
5. dissolutionwas dissolved in Methanol (100 mL)
6. temperaturethe mixture was heated
7. temperatureat reflux for 3 hrs
8. custompartitioned between ethyl acetate (200 mL) and 1N aqueous NaHCO3 (50 mL)
9. washThe separated organic layer was washed with brine
10. dry with materialdried over Na2SO4
11. customevaporated to dryness, which
12. customwas purified by silica gel chromatography
13. washeluted with PE

ORDレコード

ord-c5b139a6c5534cccacd51b330156fa06

出典データセット

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US09012642B2