CHEM01200604012 Dibakar Goswami - Homi Bhabha National ...

31.6, 32.2, 63.4, 128.8, 133.0. Anal. Calcd. for C 9 H 18 O: C, 76.00; H, 12.76%. Found, C,
75.78; H, 12.53%.
(Z)-Non-2-en-1-ol 77b: To a suspension of Ni(OAc) 2·4H 2 O (64.35 g, 72.5 mmol) in
anhydrous EtOH (200 mL) at 0 °C was added NaBH 4 (13.7 g, 0.37 mol) under Ar. The
reaction mixture was stirred for 20 min, ethylenediamine (50 ml) and 76 (10.16 g, 72.5
mmol) added and stirred at room temperature under a positive pressure of H 2 for an
additional 4 h. The mixture was filtrated through a Celite pad, the filtrate concentrated in
vacuo, and the residue purified by flash column chromatography on silica gel (20%
EtOAc/hexane) to give 77b. Yield: 9.06g (88%); colourless oil; IR: 3343, 969 cm -1 ; 1 H
NMR: δ 0.85 (t, J = 6.4 Hz, 3H), 1.24-1.39 (m, 8H), 1.98-2.04 (merged m with broad s,
3H), 4.03-4.21 (m, 2H), 5.42-5.62 (m, 2H); 13 C NMR: δ 13.9, 22.5, 27.3, 28.8, 29.5, 31.6,
58.3, 128.3, 132.7. Anal. Calcd. for C 9 H 18 O: C, 76.00; H, 12.76%. Found, C, 76.15; H,
12.61%.
(E) and (Z)-1-bromo-2-nonene 78a and 78b : To a cooled (0 o C) and stirred solution of
77a or 77b (7.0 g, 49.3 mmol) in Et 3 N (20 mL) was added mesyl chloride (6.20 g, 54.23
mmol) and the solution was stirred for 3 h. After completion of reaction (cf. TLC), water
and EtOAc was added to the mixture, the organic layer separated and the aqueous layer
was extracted with EtOAc. The combined organic extracts were washed with water, brine
and dried. Removal of solvent in vacuo afforded the crude product in good yield.
A mixture of the above crude product and NaBr (5.75g, 64.09 mmol) in acetone (150 mL)
was stirred for 4 h. To this reaction mixture water was added. The organic layer separated
and the aqueous layer was extracted with EtOAc. The combined organic extracts were
washed with water, brine and dried. Removal of solvent in vacuo followed by
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