Ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate → (8-Methyl-1,4-dioxaspiro(4.5)decan-8-yl)methanol

HRID 1468208Notes

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]1([C:18](OCC)=[O:19])[CH2:17][CH2:16][C:11]2([O:15][CH2:14][CH2:13][O:12]2)[CH2:10][CH2:9]1>C(OCC)C>[CH3:7][C:8]1([CH2:18][OH:19])[CH2:17][CH2:16][C:11]2([O:12][CH2:13][CH2:14][O:15]2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: 0 °C

Procedure

Under a nitrogen atmosphere, lithium aluminum hydride (31.2 mmol, 1.25 g, 2.43 eq.) was added to a stirred solution of 3(12.84 mmol, 2.93 g) in anhydrous ethyl ether (275 mL) cooled to 0° C. in an ice bath. The resulting mixture was stirred at room temperature for 1.5 hours. In order to quench remaining lithium aluminum hydride, water (2.48 mL) followed by 40% aqueous sodium hydroxide solution (1.68 mL) and additional water (3.47 mL) were successively added with stirring to the reaction mixture. The insoluble precipitate was then removed by decanting and filtration. The filtrate was dried over magnesium sulfate, filtered, and concentrated in vacuo to give 4 (12.75 mmol, 2.28 g, 99%) as a yellow oil that was used in the next reaction without further purification: 1H NMR (CDCl3) δ 3.94 (4H, s), 3.39 (2H, s), 1.68-1.35 (8H, m), 0.96 (3H, s); 13C NMR (CDCl3) δ 109.3, 71.8, 64.4, 34.5, 31.5, 30.7, 21.3.

Workup

customIn order to quench
additionwere successively added
stirringwith stirring to the reaction mixture
customThe insoluble precipitate was then removed
customby decanting
filtrationfiltration
dry with materialThe filtrate was dried over magnesium sulfate
filtrationfiltered
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-5f616f814a284f1ca09878295b781391
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09000188B2

Reaction notes

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