Toluene → HCID 11041251, compound

Temperature

100 °C

A 300 mL Parr bomb was charged with 10.0 g of 2-iodobenzyl alcohol (Aldrich), 80 mL of toluene, 30 mL of cyclopentene (Aldrich), 2.60 g of tri-ortho-tolylphosphine (Aldrich), and 6.6 mL of Et3N. The mixture was deoxygenated by bubbling N2 through for 10 min and was then treated with 0.96 g of Pd(OAc)2 (Aldrich). The bomb was flushed with N2, sealed, and heated to 100° C. for 18 h. The vessel was cooled to RT, purged with N2 and opened. The dark red reaction mixture was concentrated in vacuo to give a red-brown syrup. This material was dissolved in 200 mL of CH2Cl2, washed with water (4×100 mL), dried over anhydrous MgSO4, and concentrated in vacuo to afford a brown oil. Analysis by tlc (SiO2, 8:2 hexane:EtOAc) indicated two new major components at Rf =0.45 and 0.50, tri-o-tolyphosphine at Rf =0.90, and 4 minor components at Rf =0.60, 0.70, 0.85 and 0.0. The crude product was purified by flash chromatography (twice) on 200 g of silica gel (9:1 hexane:EtOAc) to afford 6:1 g (82%) of a mixture of the Rf =0.45 and 0.50 materials. This material was determined to be a mixture of double bond isomers by 1H-NMR. The product (6.0g ) was then hydrogenated at 40 psi in 40 mL of MeOH in the presence of 0.60 g of 5% Pt(C) (Aldrich) for 4 h. The catalyst was removed by filteration through celite and the filtrate was concentrated in vacuo to afford 5.47 g (74% from 2-iodobenzyl alcohol) of 2-cyclopentylbenzyl alcohol as a light yellow-brown liquid.

1. customThe mixture was deoxygenated
2. customby bubbling N2 through for 10 min
3. additionwas then treated with 0.96 g of Pd(OAc)2 (Aldrich)
4. customThe bomb was flushed with N2
5. customsealed
6. temperatureThe vessel was cooled to RT
7. custompurged with N2
8. customThe dark red reaction mixture
9. concentrationwas concentrated in vacuo
10. customto give a red-brown syrup
11. washwashed with water (4×100 mL)
12. dry with materialdried over anhydrous MgSO4
13. concentrationconcentrated in vacuo
14. customto afford a brown oil
15. customThe crude product was purified by flash chromatography (twice) on 200 g of silica gel (9:1 hexane:EtOAc)
16. customto afford 6
17. additiona mixture of double bond isomers by 1H-NMR
18. customThe catalyst was removed by filteration through celite
19. concentrationthe filtrate was concentrated in vacuo

ORD record

ord-9eb70ad64e684c7789b994b2896df74c

Source dataset

uspto-grants-2000_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06140100