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

HRID 2168135Notes

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>O1CCCC1>[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

In a 500 ml, round-bottomed flask was lithium aluminum hydride (1.772 g) in tetrahydrofuran (234 mL) to give a suspension. This suspension was cooled to 0° C. and ethyl 8-methyl-1,4-dioxaspiro[4.5]decane-8-carboxylate (10.66 g) was added via addition funnel. The reaction was stirred overnight at room temperature and then cooled back down to 0° C. The excess lithium aluminum hydride was slowly quenched with 1.8 mL water, 1.8 mL aqueous NaOH (5N) and 5.6 mL water. The suspension was stirred until the salts turned white and was then filtered through a plug of silica gel. The filtrate was concentrated by rotary evaporation and the residue was purified by regular phase flash column chromatography (Analogix, 0-75% hexanes/ethyl acetate).

Workup

customto give a suspension
temperaturecooled back down to 0° C
customThe excess lithium aluminum hydride was slowly quenched with 1.8 mL water, 1.8 mL aqueous NaOH (5N) and 5.6 mL water
stirringThe suspension was stirred until the salts
filtrationwas then filtered through a plug of silica gel
concentrationThe filtrate was concentrated by rotary evaporation
customthe residue was purified by regular phase flash column chromatography (Analogix, 0-75% hexanes/ethyl acetate)

Sources & evidence

ORD record: ord-6c4046d4314b46e59efc72f037503119
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09045475B2

Reaction notes

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