Ethanol → (Z)-Methyl 3-Methylhepta-2,6-dienoate

Temperature

-20 °C

A suspension of copper(I) iodide (12.38 g, 65 mmol) in 150 mL of dry THF under a nitrogen atmosphere was cooled to −20° C., and methyllithium (1.6 M in ether, 81.5 mL, 130 mmol) was added dropwise over 15 min. The solution was cooled to −78° C., and 4.49 g (32.5 mmol) of the compound from Example 19 in 15 mL of dry THF was added gradually, keeping the temperature below −70° C. After 1 h, 40 mL of ethanol was added cautiously, and the mixture was allowed to warm to room temperature. The mixture was diluted with ether, and washed with satd aq NH4Cl (200 mL), 5N NH3 (4×250 mL), water (200 mL), and brine (200 mL), dried, and the bulk of the solvent was evaporated to give the title compound (6.8 g, 100%) as an oil. The material had only minor solvent contamination and was adequate for use in the next reaction.

1. temperatureThe solution was cooled to −78° C.
2. customthe temperature below −70° C
3. temperatureto warm to room temperature
4. washwashed with satd aq NH4Cl (200 mL), 5N NH3 (4×250 mL), water (200 mL), and brine (200 mL)
5. customdried
6. customthe bulk of the solvent was evaporated

ORD record

ord-eb59f0ed371d4fb4b3b0354ea76a7b3d

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08039465B2