Nitrogen → HCID 12508227, compound

3 g of 1-hexene and 22 g of THF were passed into the reactor tube with a 30 ml/min flow of N2. The reaction mixture was washed with 150 ml of 1:1 v/v water/ether to separate the 1 g. of water soluble THF dimer 2-(1-methyl-pentyl)-tetrahydrofuran which was formed. The organic phase was chromatographed on silica gel. Elution with 5% ether and 5% petroleum ether in cyclohexane to yield material which was shown to be 96% pure title compound by GC. 250 MHz 13C-NMR (CDCl3 ; data for d,l for meso mixture): 13.88 (q, 2C), 14.84 (q, IC), 15.40 (q, IC), 22.73 (t, 2C), 25.65 (t, lC), 25.75 (t, IC), 28.39 (t, lC), 28.74 (t, lC), 29.00 (t, IC), 29.15 (t, IC), 32.54 (t, IC), 33.13 (t, IC), 37.66 (d, 2C), 67.52 (t, 2C), 83.60 (d, 2C).

1. washThe reaction mixture was washed with 150 ml of 1:1 v/v water/ether
2. customto separate the 1 g
3. customof water soluble THF dimer 2-(1-methyl-pentyl)-tetrahydrofuran which was formed
4. customThe organic phase was chromatographed on silica gel
5. washElution with 5% ether and 5% petroleum ether in cyclohexane
6. customto yield material which

ORD record

ord-a55a00ad71854b5caa9f397d68676bd8

Source dataset

uspto-grants-1992_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05104503