Aluminium lithium hydride → 3-(5-Fluoro-2-methoxyphenyl)-3-methylbutan-1-ol

HRID 2106051Notes

Reaction equation

HRID 2106051 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][C:8]([C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])([CH3:14])[CH2:9][C:10](OC)=[O:11]>C1COCC1>[CH3:14][C:8]([C:15]1[CH:20]=[C:19]([F:21])[CH:18]=[CH:17][C:16]=1[O:22][CH3:23])([CH3:7])[CH2:9][CH2:10][OH:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57809938Methyl 3-methyl-3-(2-methoxy-5-fluorophenyl)butanoate

Product 1

HCID 578097383-(5-Fluoro-2-methoxyphenyl)-3-methylbutan-1-olYield 89%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (0.75 g) in THF (20 mL) stirred under nitrogen was added dropwise a solution of methyl 3-methyl-3-(2-methoxy-5-fluorophenyl)butanoate (4.2 g) dissolved in THF (10 mL). The mixture was stirred at room temperature for 4 hours. The reaction was quenched by cautious addition of water (1 mL) and diluted with ether (100 mL). The mixture was filtered through FLORISIL® selective adsorbent and evaporated to dryness in vacuo to give 3-methyl-3-(2-methoxy-5-fluorophenyl)butan-1-ol as an oil (3.30 g, 89%).

Workup

  1. stirringThe mixture was stirred at room temperature for 4 hours
  2. customThe reaction was quenched by cautious addition of water (1 mL)
  3. additiondiluted with ether (100 mL)
  4. filtrationThe mixture was filtered through FLORISIL® selective adsorbent
  5. customevaporated to dryness in vacuo

Sources & evidence

ORD record
ord-631a42eb788b47559a86215fda2ee0f7
Source dataset
uspto-grants-2009_08
Patent number
US07579469B2

Reaction notes

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