Methyl iodide → HCID 60026352, compound

To a solution of 2-methyl-2-phenylpent-4-en-1-ol (3.2 g, 18.15 mmol) in 17 mL of DMF was added sodium hydride (1.25 g, 31.25 mmol, 60% in mineral oil). The mixture was stirred until foaming ceased and then methyl iodide (6 mL, 96 mmol) was added. After 2 hours, the mixture was quenched with 50 mL of saturated aqueous ammonium chloride solution and extracted with three 50 mL portions of ethyl acetate. The combined organic layers were washed with 30 mL of saturated aqueous ammonium chloride solution, five 25 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo to afford 3.4 g (98.4% yield) of (1-methoxymethyl-1-methylbut-3-enyl)benzene which was used without further purification.

1. customthe mixture was quenched with 50 mL of saturated aqueous ammonium chloride solution
2. extractionextracted with three 50 mL portions of ethyl acetate
3. washThe combined organic layers were washed with 30 mL of saturated aqueous ammonium chloride solution, five 25 mL portions of brine
4. dry with materialdried over magnesium sulfate
5. filtrationfiltered
6. concentrationconcentrated in vacuo

ORD record

ord-1759b24fe55b4439a0f5b7ed36b2830d

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741897B2