Sodium sulfate decahydrate → 2-Methyl-2-(2-methylquinolin-8-yl)propan-1-ol

HRID 338906Notes

Reaction equation

[CH3:1][C:2]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH3:18])[CH:14]=[CH:13]2)([CH3:7])[C:3](OC)=[O:4].[H-].[H-].[H-].[H-].[Li+].[Al+3].O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:7][C:2]([C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:17]=1[N:16]=[C:15]([CH3:18])[CH:14]=[CH:13]2)([CH3:1])[CH2:3][OH:4]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of methyl 2-methyl-2-(2-methylquinolin-8-yl)propanoate (0.57 g, 2.3 mmol) in THF (10 mL) was added 1 N LAH (5.9 mL, 5.9 mmol) in THF at 0° C. and stirred at 0° C. for 6 hours. Sodium sulfate decahydrate (2.0 g) was added and the reaction mixture was stirred at ambient temperature for 30 minutes. The solid was removed by filtration and washed with ethyl acetate (30 mL). The filtrate was concentrated under reduced pressure and the residue was purified by flash chromatography on silica gel (1:1 hexane/ethyl acetate) to give 2-methyl-2-(2-methylquinolin-8-yl)propan-1-ol (0.43 g, 85%) as an oil.

Workup

stirringthe reaction mixture was stirred at ambient temperature for 30 minutes
customThe solid was removed by filtration
washwashed with ethyl acetate (30 mL)
concentrationThe filtrate was concentrated under reduced pressure
customthe residue was purified by flash chromatography on silica gel (1:1 hexane/ethyl acetate)

Sources & evidence

ORD record: ord-e7f3f4e6e1a24344a3ee18d971539c0b
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889704B2

Reaction notes

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