Tetramethyltin → 2-Butyl-5-methoxy-4-methyl-1-indanone

Temperatur

100 °C

A solution of 4-bromo-2-butyl-5-methoxy-1-indanone (1.159 g, 3.90 mmol) in anhydrous dimethylformamide (39 mL) was treated with LiCl (455 mg, 10.73 mmol), PPh3 (205 mg, 0.78 mmol), PdCl2(PPh3)2 (205 mg, 0.292 mmol) and Me4Sn (1.08 mL, 7.80 mmol). The mixture was placed under a nitrogen atmosphere, then stirred and heated in an oil bath at 100° C. for 16.5 hours. After cooling to room temperature, the mixture was diluted with water (100 mL) and extracted with Et2O (100 mL, 2×25 mL). The ether extracts were washed with brine, dried over MgSO4, filtered and evaporated under vacuum to a yellow solid (1.29 g). This material was purified by chromatography on EM silica gel 60 (230-400 mesh, 130 mL dry, packed under CH2Cl2), using CH2Cl2 as eluting solvent, to afford a 92:3:5 mixture (0.90 g) of 2-butyl-5-methoxy-4-methyl-1-indanone, the 6-methyl isomer, and the desmethyl product. This material was used as is in the next step.

1. temperatureAfter cooling to room temperature
2. extractionextracted with Et2O (100 mL, 2×25 mL)
3. washThe ether extracts were washed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customevaporated under vacuum to a yellow solid (1.29 g)
7. customThis material was purified by chromatography on EM silica gel 60 (230-400 mesh, 130 mL dry, packed under CH2Cl2)
8. washas eluting solvent

ORD-Eintrag

ord-16948c22a2304cf0b6f9a96bed7293bb

Quelldatensatz

uspto-grants-2006_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07087599B2