Diiodomethane → 1-Trimethylsiloxybicyclo[4.1.0]heptane

Temperature

0 °C

Diiodomethane(120 μl, 1.5 mmol) was added slowly to perfluorohexanes (FC-72, 3 mL) in a test tube (14 mm×105 mm) and then trimethylsiloxycyclohexene (180 mg, 1.05 mmol) in hexane (3.5 mL) was slowly poured into the test tube. A hexane solution of diethylzinc (1.0 M, 1.5 mmol, 1.5 mmol) was added to the hexane layer, and the diiodomethane layer on the bottom was stirred gently so as not to mix the three phases. After 10 h at room temperature, additional diidomethane (40 μl, 0.5 mmol) was added to the bottom layer of the test tube by using a syringe. After 14 h, the reaction mixture was cooled to 0° C., and saturated NH4Cl (10 mL) was added. The hexane layer was decanted, washed with H2O, dried over MgSO4, and concentrated in vacuo. The residue was purified by short column chromatography (17 mm×20 mm of florisil layer over 50 mm of silica gel layer) with benzene/hexane: ¼ to give 1-trimethylsiloxybicyclo[4.1.0]heptane in 63% yield (123 mg).

1. additionto mix the three phases
2. additionadditional diidomethane (40 μl, 0.5 mmol) was added to the bottom layer of the test tube
3. waitAfter 14 h
4. customThe hexane layer was decanted
5. washwashed with H2O
6. dry with materialdried over MgSO4
7. concentrationconcentrated in vacuo
8. customThe residue was purified by short column chromatography (17 mm×20 mm of florisil layer over 50 mm of silica gel layer) with benzene/hexane

ORD record

ord-92a0f2960a1748639a894db00f443c92

Source dataset

uspto-grants-2005_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06897331B2