Triphenylphosphine → 10-Chloro-1-decene

To a flame-dried round-bottomed flask was added PPh3 (1.1 equiv, 27.5 mmol, 7.21 g) and THF (65 mL). N-chlorosuccinimide (1.1 equiv, 27.5 mmol, 3.67 g) was dissolved in THF (50 mL) and added dropwise. The mixture was stirred for 5 min, and 9-decen-1-ol (1 equiv, 25 mmol, 3.91 g) was added dropwise in THF (30 mL). After 9 h, the volatile components of the reaction were evaporated and hexanes (100 mL) and H2O (50 mL) were added. The liquid was decanted and the resulting solid was washed with hexanes. The aqueous layer was collected and extracted with hexanes (2×50 mL). The combined organic layers were washed sequentially with bleach (30 mL) and brine (50 mL). The crude product was filtered through a pad of silica (which was washed with ˜400 mL of hexanes) and concentration in vacuo to afford 10-chlorodecene (3.48 g, 20 mmol, 80%), which was deemed pure by NMR and used without further purification. TLC Rf=0.87 (5% EtOAc/Hex); 1HNMR (400 MHz): δ 5.84 (ddt, 1H, J=17.4, 10.3, 6.7 Hz), 5.02 (ddd, 1H, J=17.4, 2.0, 3.6 Hz), 4.93-4.98 (m, 1H), 3.56 (t, 2H, J=6.5 Hz), 2.02-2.12 (m, 2H), 1.74-1.84 (2H), 1.27-1.50 (10H); 13CNMR (100 MHz): δ 139.2, 114.2, 45.2, 33.8, 32.7, 29.3, 29.0, 28.88, 28.85, 26.88.

1. additionadded dropwise
2. waitAfter 9 h
3. customthe volatile components of the reaction were evaporated
4. additionhexanes (100 mL) and H2O (50 mL) were added
5. customThe liquid was decanted
6. washthe resulting solid was washed with hexanes
7. customThe aqueous layer was collected
8. extractionextracted with hexanes (2×50 mL)
9. washThe combined organic layers were washed sequentially with bleach (30 mL) and brine (50 mL)
10. filtrationThe crude product was filtered through a pad of silica (which was washed with ˜400 mL of hexanes) and concentration in vacuo

ORD record

ord-2c0572136586425db590188931c73548

Source dataset

uspto-grants-2015_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09079835B2