Cyclopentadecanolide synthesis
- Product Name:Cyclopentadecanolide
- CAS Number:106-02-5
- Molecular formula:C15H28O2
- Molecular Weight:240.38
76529-42-5
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106-02-5
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Yield:106-02-5 88%
Reaction Conditions:
with Lipase B immobilized on acrylic resin from Candida antarctica in cyclohexane;water at 40; for 2 h;Enzymatic reaction;
Steps:
4.3 Synthesis of exaltolide (3)
The reaction vessel containing a suspension of 50mg of enzyme CALB (lipase B acrylic resin from C. antarctica (EC 3.1.1.3, 10,000U/g) in 40mL of cyclohexane was placed in a closed chamber containing a saturated solution of salt hydrates (Na2HPO4·7H20/2H20) and kept overnight in indirectly contact, under vigorous agitation. Then, hydroxyester 4 (11.0mg, 0.04mmol) was added and the reaction was vigorously stirred at 40°C for 2h. At the end, the enzyme was removed by filtration and the filtrate was concentrated under vacuum. Purification of the crude material on flash column chromatography, eluting with hexane/chloroform 6/4, afforded exaltolide (3) (8.5mg, 88%) as colourless oil. Exaltolide (3): Rf (50% CHCl3/hexane) 0.66; IR (CHCl3): 2934, 1736, 1344cm-1; 1H NMR (CDCl3, 300MHz): δ 4.13 (2H, t, J=5.6Hz), 2.33 (2H, t, J=6.6Hz), 1.72-1.60 (4H, m), 1.43-1.29 (20H, m). 13C NMR (100MHz CDCl3): δ 174.0 (C), 63.9 (CH2), 34.4 (CH2), 28.3 (CH2), 27.7 (CH2), 27.1 (2 CH2), 26.8 (CH2), 26.6 (CH2), 26.3 (CH2), 26.0 (CH2), 25.9 (CH2), 25.8 (CH2), 25.1 (CH2), 24.9 (CH2). ES-MS (m/z): 263 [M+Na]+, 241 [M+H]+. Anal. Calcd for C15H28O2: C, 74.95; H, 11.74. Found: C, 74.81; H, 11.48.
References:
Fortunati, Tancredi;D'Acunto, Mariantonietta;Caruso, Tonino;Spinella, Aldo [Tetrahedron,2015,vol. 71,# 16,art. no. 26489,p. 2357 - 2362]
87227-39-2
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106-02-5
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4617-33-8
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502-72-7
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63294-84-8
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106-02-5
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