HCID 21261661, compound → HCID 21261646, compound

Participants

Reaction Steps

5.04 g of 2-(8,8-Dibromo-5,5-dimethyl-oct-7-enyloxy)-tetrahydro-pyrane (example1/step i]) (12.66 mmol) was dissolved in 55 ml of abs. tetrahydrofuran and treated at −78° with 25.3 ml of n-butyllithium (1.5 M, hexane, 3 eq.). 30 Min. later, the reaction mixture was poured onto crushed ice/NH4Cl, extracted twice with ether, washed with brine, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, hexane/ethylacetate=95/5) gave 3.07 g of 2-(5,5-dimethyl-oct-7-ynyloxy)-tetrahydro-pyrane which was deprotected as follows: 2.00 g thereof (8.39 mmol) was dissolved in 57 ml of methanol, treated with 211 mg of pyridinium-(toluene-4-sulfonate) (0.1 eq.), and kept at room temperature for 1 night. The reaction mixture was then poured onto crushed ice/Na2CO3, extracted twice with ether, washed with water, dried over sodium sulfate and evaporated to dryness. Flash chromatography (SiO2, pentane/methylacetate=75/25) gave 1.27 g of the title compound as colourless oil, 99% pure according to GC.

Provenance & Evidence