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3-Ethyl-3-methyl-pentanoic acid methyl ester → 3-Ethyl-3-methylpentan-1-ol

HRID 1806947
Notes
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Reaction equation

HRID 1806947 reaction equation
C[O:2][C:3](=O)[CH2:4][C:5]([CH2:9][CH3:10])([CH3:8])[CH2:6][CH3:7].[H-].[H-].[H-].[H-].[Li+].[Al+3]>O1CCCC1>[CH2:6]([C:5]([CH3:8])([CH2:9][CH3:10])[CH2:4][CH2:3][OH:2])[CH3:7]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 134430493-Ethyl-3-methyl-pentanoic acid methyl esterHCID 21226445Aluminium lithium hydride

Product 1

HCID 234649203-Ethyl-3-methylpentan-1-olYield 106.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Step C To a solution of 3-ethyl-3-methyl-pentanoic acid methyl ester (1.5 g, 9.4 mmol) in anhydrous tetrahydrofuran (30 mL) at 0° C. was added a tetrahydrofuran solution (2 M) of LiAlH4 (5 mL, 10 mmol) under nitrogen. The reaction mixture was stirred at 0° C. for 1 h, then poured into a ice-water. The mixture was extracted with ethyl acetate. The organic layer were separated, washed with water, aqueous HCl solution, brine, dried over MgSO4, and concentrated to give 3-ethyl-3-methyl-pentan-1-ol as a yellow oil (1.3 g, 100%).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. customThe organic layer were separated
  3. washwashed with water, aqueous HCl solution, brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-5256f048a87a4846a46f356737f1ef70
Source dataset
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08354444B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes