5
38
Mane, Kadam:
above to give th e crude product wh ich was purified by TLC (silica gel G, petroleum
eth er–eth yl acetate, 9 : 1). Th e yield of pure occidol (1) was 0.30 g (79%), m .p. 97–98 °C (pe-
9
1
troleum eth er) (ref. gives m .p. 99–100 °C). IR (KBr): 3 420 (broad, OH). H NMR (CDCl ):
3
1
.23 s, 6 H (CH ); 1.4 bs, 1 H (OH); 2.15 s, 3 H (Ar-CH ); 2.2 s, 3 H (Ar-CH ); 1.6 m , 2 H
3 3 3
(
CH ); 2.1 m , 1 H (CH); 2.65 m , 4 H (CH ); 6.73 an d 6.77 AB quartet, 2 H, J = 8.5 (Ar-H). For
2 2
C15H22O (218.3) calculated: 82.53% C, 10.15% H; foun d: 82.48% C, 9.92% H.
B) To a stirred solution of m eth yllith ium , prepared from lith ium (0.29 g, 41.7 m m ol) an d
m eth yl iodide (1.34 m l, 21.5 m m ol) in dry eth er (80 m l), a solution of 11 (0.61 g, 3 m m ol)
in dieth yl eth er (10 m l) was added durin g 15 m in . Th e reaction was carried out as described
above to give th e crude product wh ich was purified by TLC (silica gel G, petroleum
eth er–eth yl acetate, 9 : 1). Th e yield of pure 1 was 0.51 g (77%).
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2
Collect. Czech. Chem. Commun. (Vol. 64) (1999)