Tributylstannane → Stannane, tributyl(methoxymethyl)-

n-Butyl lithium (2.4 M, n-hexane solution, 25 mL, 61 mmol) was dropped into a mixture of diisopropylamine (9.4 mL, 67 mmol) and tetrahydrofuran (150 mL) at −78° C. followed by stirring for 30 minutes at the same temperature. Tributyl tin hydride (16 mL, 61 mmol) was dropped in at the same temperature followed by stirring for 30 minutes while cooling with ice. The reaction mixture was brought to a temperature of −78° C. followed by dropping in chloromethyl methyl ether (4.6 mL, 61 mmol) and gradually warming to room temperature. Water (100 mL) was added to the reaction mixture followed by extraction with diethyl ether (300 mL). After washing the organic layer with sat. NaCl, the organic layer was distilled under a reduced pressure. The residue was purified by neutral silica gel column chromatography (heptane/ethyl acetate=30/1) to obtain the title compound (18 g, 0.52 mmol, 86%) as a colorless oil.

1. stirringby stirring for 30 minutes
2. temperaturewhile cooling with ice
3. customwas brought to a temperature of −78° C.
4. extractionfollowed by extraction with diethyl ether (300 mL)
5. washAfter washing the organic layer with sat. NaCl
6. distillationthe organic layer was distilled under a reduced pressure
7. customThe residue was purified by neutral silica gel column chromatography (heptane/ethyl acetate=30/1)

ORD record

ord-75e742729a4d46c59ee9f94a40f326c9

Source dataset

uspto-grants-2010_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07829585B2