3-Cycloocten-1-ol synthesis

6synthesis methods

Product Name:3-Cycloocten-1-ol
CAS Number:4114-99-2
Molecular formula:
Molecular Weight:0

9-Oxabicyclo[6.1.0]non-2-ene, (1R-cis)- (9CI)

183904-03-2
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Yield:4114-99-2 77%

Reaction Conditions:

with lithium aluminium tetrahydride in tetrahydrofuran at 0 - 20;Inert atmosphere;

Steps:

4

A solution of LiAlH₄(0.5 eq., 81.5 ml of a 1.0 M solution in THF, 81.5 mmol) was added dropwise at 0° C. and under Ar to a stirred solution of 17 (1.0 eq., 20.23 g, 163 mmol) in THF (1.0 M, 163 ml). The reaction mixture was allowed to warm up to rt and stirred o/n. H₂O (about 20 ml) was carefully added to stop the reaction. The reaction mixture was filtered, dried over Na₂SO₄, and concentrated. FC (20% EtOAc in C₆H₁₂) yielded 18 (15.81 g, 125 mmol, 77%) as a clear liquid. (0803) R_f(20% EtOAc in C₆H₁₂)=0.4. (0804) ¹H-NMR (CDCl₃) δ=5.76-5.60 (m, 2H), 3.84-3.77 (m, 1H), 2.36 (dd, ³J(H,H)=7.5, 6.3 Hz, 2H), 2.28-2.18 (m, 1H), 2.14-2.05 (m, 1H), 1.87-1.78 (m, 1H), 1.73-1.63 (m, 1H), 1.61-1.43 (m, 4H), 1.40-1.30 (m, 1 H) ppm. (0805) ¹³C-NMR (CDCl₃) δ=132.4, 125.0, 72.2, 35.1, 34.0, 28.3, 25.7, 21.2 ppm.

References:

US2016/340297,2016,A1 Location in patent:Paragraph 0802-0805

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14916-79-1
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$40.21/5g

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