1,4-Dioxaspiro[4.5]decan-8-one → 8-Methyl-1,4-dioxaspiro(4.5)decan-8-ol

HRID 1500884Notes

Reaction equation

[O:1]1[C:5]2([CH2:10][CH2:9][C:8](=[O:11])[CH2:7][CH2:6]2)[O:4][CH2:3][CH2:2]1.[CH3:12][Li]>C1COCC1>[CH3:12][C:8]1([OH:11])[CH2:7][CH2:6][C:5]2([O:4][CH2:3][CH2:2][O:1]2)[CH2:10][CH2:9]1

Participants

Conditions

Temperature: -55 °C

Procedure

To a cooled solution of 1,4-dioxaspiro[4.5]decan-8-one (7.8 g, 50.0 mmol) in dry THF (75 mL) was added methyllithium solution (1.5 M in ether, 43.3 mL, 65.0 mmol) at −78° C. under argon while keeping inner temperature below −55° C. After addition, the mixture was stirred at −55° C. for additional 4 hours. The reaction was warmed to room temperature and then quenched by saturated NH4Cl solution. The separated organic layer was concentrated in vacuo and the residue was purified by column chromatography on silica gel (EA:PE=1:9 to 1:3) to afford the product as a white solid (6.8 g, yield: 80%).

Workup

customtemperature below −55° C
additionAfter addition
temperatureThe reaction was warmed to room temperature
customquenched by saturated NH4Cl solution
concentrationThe separated organic layer was concentrated in vacuo
customthe residue was purified by column chromatography on silica gel (EA:PE=1:9 to 1:3)

Sources & evidence

ORD record: ord-b1a0f7e4d65b4d109fc9e2309f48b468
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09206191B2

Reaction notes

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