Water → 2-(1,4-Dioxaspiro(4.5)decan-8-yl)ethan-1-ol

HRID 1799808

Reaction equation

[H-].[Al+3].[Li+].[H-].[H-].[H-].[O:7]1[C:11]2([CH2:16][CH2:15][CH:14]([CH2:17][C:18](OC)=[O:19])[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1.O>O1CCCC1>[O:7]1[C:11]2([CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][OH:19])[CH2:13][CH2:12]2)[O:10][CH2:9][CH2:8]1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 0.76 g of lithium aluminum hydride in 10 mL of tetrahydrofuran was cooled to 0° C. under a nitrogen atmosphere. To the suspension was added dropwise a solution of 2.18 g of methyl 1,4-dioxaspiro[4.5]decane-8-acetate in 10 mL of tetrahydrofuran, followed by stirring at room temperature for 3 hours. After the reaction mixture was cooled to 0° C., 1 mL of water was added thereto. The mixture was filtered through celite and then concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 1.73 g of 1,4-dioxaspiro[4.5]decane-8-ethanol represented by the following formula:

Workup

temperatureAfter the reaction mixture was cooled to 0° C.
filtrationThe mixture was filtered through celite
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-80fec949036d490781f7d22dab675d43
Source dataset: uspto-grants-2013_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08344163B2

Linked notes

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