Methyl iodide → 2-Cyclohexen-1-one, 4,4,6-trimethyl-

温度

23 °C

A solution of 4,4-dimethyl-cyclohex-2-en-1-one (5.00 g, 40.3 mmol, 1 equiv) in tetrahydrofuran (130 mL) was added to a solution of LHMDS (1 M in tetrahydrofuran, 58.4 mL, 58.4 mmol, 1.45 equiv) in tetrahydrofuran (60 mL) at −78° C. After stirring for 1 h, iodomethane (5.02 mL, 80.6 mmol, 2.0 equiv) was added dropwise to the flask. The cooling bath was immediately removed and the reaction mixture was allowed to warm to room temperature (23° C.). After stirring 11 h, saturated aqueous ammonium chloride solution (50 mL) and distilled water (10 mL) were added to the flask. The layers were separated and the aqueous layer was extracted with three 50-mL portions of ether. The combined organic layers were washed once with brine (10 mL) and dried over sodium sulfate (15 min). Following filtration, volatiles were removed in vacuo, leaving a brown residue which was distilled at 22 torr furnishing 4,4,6-trimethyl-cyclohex-2-en-1-one (10, 3.93 g, 72%) as a clear oil, bp 82-86° C. (Torri, J.; Azzaro, M. Bull. Soc. Chem. Fr. 1978, 283; incorporated herein by reference).

1. customThe cooling bath was immediately removed
2. stirringAfter stirring 11 h
3. distillationsaturated aqueous ammonium chloride solution (50 mL) and distilled water (10 mL)
4. additionwere added to the flask
5. customThe layers were separated
6. extractionthe aqueous layer was extracted with three 50-mL portions of ether
7. washThe combined organic layers were washed once with brine (10 mL)
8. dry with materialdried over sodium sulfate (15 min)
9. filtrationfiltration, volatiles
10. customwere removed in vacuo
11. customleaving a brown residue which
12. distillationwas distilled at 22 torr

ORDレコード

ord-71b73fe2966f434d85af853d7188a634

出典データセット

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07902196B2