Benzaldehyde → HCID 9989768, compound

Temperature

-78 °C

4-Chloro-2-methyl-2-butene (3.2 mmol) was weighed into a vial and sealed with a septum. Using a freeze-pump-thaw technique, air was removed and replaced with argon. THF (4 ml) was added to the vial and then cooled to -78° C. The allyl chloride was then cannulated to the active coppersolution (8.00 mmol) at -108° C. The solution was stirred at -108° C. for 10 minutes and then warmed to -78° C. Benzaldehyde (1.60 mmol) and decane (3.20 mmol) were admixed with 4 ml of THF in a vial, cooled to -78° C. and then cannulated to the organocopper solution at -78° C. and stirred for 30 minutes. The solution was then quenched with saturated NH4Cl(aq), extracted with ether (3×20 ml), washed with brine (3×50 ml), and the organic layer dried over MgSO4. Flash silica gel chromatography usinggradient mixtures of hexanes/EtOAc afforded 2,2-dimethyl-1-phenyl-3-butene-1-ol (1.28 mmol), for an 80% yield: IR (neat) 3451, 3083, 3062, 3029, 2964, 2929, 2869, 1637, 1452, 1413, 1378, 1361, 1187, 1024, 998, 730, 701. 1H NMR (300 MHz) 7.24-7.28 (m, 5H),5.84-5.93 (dd, J1 =17.41 Hz, J2 =10.73 Hz, 1H), 5.00-5.12 (m, 2H), 4.37 (s, 1H), 2.23 (s, 1H), 0.98 (s, 3H), 0.93 (s, 3H). 13C NMR(300 MHz) 144.9, 140.6, 127.7, 127.3, 113.6, 80.4, 42.0, 24.2, 20.9.

1. customsealed with a septum
2. customwas removed
3. additionTHF (4 ml) was added to the vial and
4. customwas then cannulated to the active coppersolution (8.00 mmol) at -108° C
5. temperaturewarmed to -78° C
6. temperaturecooled to -78° C.
7. stirringstirred for 30 minutes
8. customThe solution was then quenched with saturated NH4Cl(aq)
9. extractionextracted with ether (3×20 ml)
10. washwashed with brine (3×50 ml)
11. dry with materialthe organic layer dried over MgSO4

ORD record

ord-f97186bea75b44929861e090f32654f5

Source dataset

uspto-grants-1996_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05490952