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Sodium sulfate decahydrate → 3-Methyl-3-(2-methylquinolin-8-yl)butan-1-ol

HRID 339039
Notes
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Reaction equation

HRID 339039 reaction equation
[CH3:1][C:2]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([CH3:20])[CH:16]=[CH:15]2)([CH3:9])[CH2:3][C:4](OCC)=[O:5].[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>[CH3:9][C:2]([C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:19]=1[N:18]=[C:17]([CH3:20])[CH:16]=[CH:15]2)([CH3:1])[CH2:3][CH2:4][OH:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 62649Sodium sulfate decahydrateHCID 21226445Aluminium lithium hydrideHCID 70984548Ethyl 3-methyl-3-(2-methylquinolin-8-yl)butanoate

Product 1

HCID 709836813-Methyl-3-(2-methylquinolin-8-yl)butan-1-olYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent
2×

Conditions

Temperature
0 °C

Procedure

To a solution of ethyl 3-methyl-3-(2-methylquinolin-8-yl)butanoate (0.66 g, 2.43 mmol) in THF (3 mL) was added 1.0 N LAH (3.65 mL, 3.65 mmol) in THF at 0° C. and stirred at 0° C. for 3 hours. Sodium sulfate decahydrate (2.0 g) was added and 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 to give 3-methyl-3-(2-methylquinolin-8-yl)butan-1-ol (0.56 g, 100%) as a solid.

Workup

  1. stirringstirred at ambient temperature for 30 minutes
  2. customThe solid was removed by filtration
  3. washwashed with ethyl acetate (30 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-23c707aa913b48f2a10d83ad28b916af
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08889704B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes