2-Cyclohexen-1-ol, 2,4,4-trimethyl- synthesis
- Product Name:2-Cyclohexen-1-ol, 2,4,4-trimethyl-
- CAS Number:134736-78-0
- Molecular formula:C9H16O
- Molecular Weight:140.22
13395-71-6
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Yield:134736-78-0 94%
Reaction Conditions:
with methanol;sodium tetrahydroborate;cerium(III) chloride heptahydrate at 0; for 0.5 h;Luche Cerium Reduction;
Steps:
2, 4, 4-Trimethylcyclohex-2-en-1-ol (15)3
To a solution of 2,4,4-trimethylcyclohex-2-en-1-one (4) (2.3 g, 17 mmol) and cerium (III) chloride heptahydrate (7.1 g, 19 mmol) in methanol (50 mL) at 0 °C was added sodium borohydride (0.69 g, 18 mmol) portion-wise over 20 minutes with stirring. The reaction mixture was left to react for a further 10 minutes and then solvent was removed in vacuo. The residue was diluted with diethyl ether (10 mL), followed by addition of 1 M aqueous hydrochloric acid (10 mL) until a clear solution was obtained. The organic layer was collected and the aqueous layer washed with diethyl ether (3 x 40 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate (100 mL) and brine (100 mL), dried (Na2SO4) and solvent removed in vacuo. The crude product was purified by column chromatography eluting in 10 % ethyl acetate in hexanes to give 15 (2.2 g, 16 mmol, 94%) as a pale-yellow oil. 1H NMR (400 MHz, CDCl3): δ 5.20 (s, 1 H), 3.90 (t, 1 H, J = 5.0), 1.84 (dddd, 2 H, J = 13.8, 10.6, 4.8, 3.3), 1.71 (s, 3 H), 1.68 (dddd, 1 H, J = 13.7, 7.6, 5.0, 3.3), 1.50 (ddd, 1 H, J = 13.4, 10.6, 3.3), 1.35 (ddd, 1 H, J = 13.3, 7.5, 3.3), 0.96 (s, 3 H), 0.90 (s, 3 H); 13C NMR (101 MHz, CDCl3): δ 136.0, 132.9, 68.6, 32.9, 32.2, 30.0, 29.4, 28.6, 20.5; IR (film, cm-1): 3327, 3024, 2933, 2861, 2836, 1450, 1435, 1387, 1283, 1048, 1002.
References:
Kikuchi, Kai;McErlean, Christopher S.P. [Tetrahedron Letters,2021,vol. 70,art. no. 153003] Location in patent:supporting information
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