1,2-Cyclohexanedione → Methyl 3-acetyl-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate

HRID 240872

Reaktionsgleichung

[O:1]=[C:2]([CH3:10])[CH2:3][S:4][CH2:5][C:6]([O:8][CH3:9])=[O:7].[Na].[C:12]1(=O)[CH2:17][CH2:16][CH2:15][CH2:14][C:13]1=O>CO>[C:2]([C:3]1[S:4][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:13]2[CH2:14][CH2:15][CH2:16][CH2:17][C:12]=12)(=[O:1])[CH3:10]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

Add methyl 2-(2-oxopropylthio)acetate (35.4 g, 183.2 mmol) to a freshly prepared solution of solid sodium (8.78 g, 381.5 mmol) in dry MeOH (300 mL) at 0° C., followed by addition of a solution of cyclohexane-1,2-dione (20 g, 152.6 mmol) in MeOH (30 mL). Stir the mixture at 0° C. for 30 min and then at 50-60° C. for additional 1.5 hour. Remove the solvent under vacuum and dilute the residue with water (100 mL). Extract the aqueous mixture with ethyl acetate (100 mL×3). The combined organic layers are washed with brine, dried over anhydrous Na2SO4, and evaporated under vacuum. Purify the residue by a flash column on silica gel eluting with PE:EtOAc (50:1 to 30:1) to afford methyl 3-acetyl-4,5,6,7-tetrahydrobenzo[c]thiophene-1-carboxylate as a white solid (10 g, 27.6%). MS (m/z): 239 (M+1).

Aufarbeitung

waitat 50-60° C. for additional 1.5 hour
customRemove the solvent under vacuum
additiondilute the residue with water (100 mL)
extractionExtract the aqueous mixture with ethyl acetate (100 mL×3)
washThe combined organic layers are washed with brine
dry with materialdried over anhydrous Na2SO4
customevaporated under vacuum
customPurify the residue by a flash column on silica gel eluting with PE

Quellen und Nachweise

ORD-Eintrag: ord-16ae45163c034151bc435fb173b7e888
Quelldatensatz: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08648081B2

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