ChemicalBook CAS DataBase List 4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE

4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE synthesis

9synthesis methods

Product Name:4,5,6,7-TETRAHYDRO-1-BENZOTHIOPHENE
CAS Number:13129-17-4
Molecular formula:C8H10S
Molecular Weight:138.23

Phosphonic acid, P-(mercaptomethyl)-, diethyl ester

70660-05-8
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1680-73-5
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$57.00/250mg

13129-17-4
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$49.20/250mg

Ethanamine, N-[(3,5-dichlorophenyl)methylene]-2,2-diethoxy-

1000210-73-0
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Yield: 49% ， 24%

Reaction Conditions:

Stage #1:diethyl (mercaptomethyl)phosphonate with sodium hydride in tetrahydrofuran at 0; for 0.25 h;
Stage #2:2-chlorocyclohexene-1-carboxaldehyde in tetrahydrofuran at 20; for 19 h;Inert atmosphere;

Steps:

Reactions of b-chloroacroleins 1a-f with diethyl mercaptomethylphosphonate:
General procedure: Toa suspension of NaH (0.024 g, 1.0 mmol) in THF (5 mL) at 0 C was addeddiethyl mercaptomethylphosphonate (0.184 g, 1.0 mmol) and the resultantsolution was stirred for 15 min. To the solution was added acrolein 1a-f(0.9 mmol) and the mixture was stirred at room temperature under an argonatmosphere (time given in Table 1). In the case of 3b, an additional portion ofNaH (0.015 g, 0.6 mmol) was added after a period of 19 h and stirring wascontinued for an additional 19 h. The solution was poured into cold H2O (orbrine in the case of 3b)/Et2O mixture (1:4, v/v, 40 mL), the organic fraction wascollected, and the aqueous fraction was extracted with Et2O (2 30 mL). Thecombined organic fractions were dried (Na2SO4) and filtered, and the solventwas removed in vacuo. The residue was chromatographed on silica gel (Et2O,100%) to afford 3a-f, 2c, d, and 5.

References:

Cal, Dariusz [Tetrahedron Letters,2014,vol. 55,# 7,p. 1332 - 1335]