Ammonium Chloride → 6-Methylhept-3-yn-1-ol

22 ml of dry tetrahydrofuran and 25 ml of a 1 Methyl magnesium bromide tetrahydrofuran solution were added to a nitrogen-substituted flask, and thereafter, 2.9 ml of 4-methylpentine was slowly added dropwise to the mixed solution. The obtained solution was stirred at a room temperature for 1 hour, and thereafter, 25 ml of a 1.1 M ethylene oxide tetrahydrofuran solution was slowly added dropwise to the reaction solution at a room temperature. The obtained solution was further stirred at a room temperature overnight. Thereafter, 100 ml of a saturated ammonium chloride aqueous solution was added to the reaction solution, and the obtained solution was then extracted with 100 ml of diethyl ether twice. It was dried over magnesium sulfate. The magnesium sulfate was filtrated, and the organic layer was then concentrated. The generated alcohol was directly used in the subsequent reaction (yield: 3.78 g).

1. stirringThe obtained solution was further stirred at a room temperature overnight
2. extractionthe obtained solution was then extracted with 100 ml of diethyl ether twice
3. dry with materialIt was dried over magnesium sulfate
4. filtrationThe magnesium sulfate was filtrated
5. concentrationthe organic layer was then concentrated
6. customThe generated alcohol was directly used in the subsequent reaction (yield: 3.78 g)

ORD record

ord-ba21869fa5ba4d218ff0367517933c48

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586505B2