Triethylamine → (Z)-Dec-4-en-1-yl methanesulfonate

To a cooled solution (0° C.) of (Z)-dec-4-en-1-ol 9 (20 g, 128.0 mmol) and triethylamine (26.7 mL, 191.9 mmol) in anhydrous dichloromethane (200 mL) was slowly added methane sulfonyl chloride (14.9 mL, 191.9 mmol). The solution was stirred for 30 min at room temperature then diluted with dichloromethane (100 mL). The solution was washed with saturated sodium bicarbonate (3×150 mL) and then the combined aqueous washes were extracted with dichloromethane (150 mL). The combined dichloromethane extracts were dried on magnesium sulfate, filtered and concentrated in vacuo to dryness. The residue was filtered through a pad of silica (100% dichloromethane) to afford (Z)-dec-4-enyl methanesulfonate 2 as a yellow oil (28.5 g, 95%). Rf 0.5 (100% CH2Cl2).

1. washThe solution was washed with saturated sodium bicarbonate (3×150 mL)
2. extractionthe combined aqueous washes were extracted with dichloromethane (150 mL)
3. dry with materialThe combined dichloromethane extracts were dried on magnesium sulfate
4. filtrationfiltered
5. concentrationconcentrated in vacuo to dryness
6. filtrationThe residue was filtered through a pad of silica (100% dichloromethane)

ORD record

ord-8b317f2f5eb341bab3c77b307320e156

Source dataset

uspto-grants-2016_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09352042B2