Aluminium lithium hydride → HCID 57810569, compound

HRID 2106481Notes

Reaction equation

HRID 2106481 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]([CH2:24][CH3:25])([C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:23])[CH:17]=3)[CH2:14][CH3:15])=[CH:10][C:9]=2[CH:26]=1)=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH2:14]([C:13]([C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([CH3:23])[CH:17]=1)([C:11]1[O:12][C:8]2[CH:7]=[CH:6][C:5]([CH2:3][OH:2])=[CH:26][C:9]=2[CH:10]=1)[CH2:24][CH3:25])[CH3:15]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57810551HCID 57810551, compound

Product 1

HCID 57810569HCID 57810569, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-[1-ethyl-1-(4-hydroxy-3-methyl-phenyl)-propyl]-benzofuran-5-carboxylic acid methyl ester (710 mg, 2.02 mmol) in THF (40 mL) at 0° C. are added with LAH (153 mg, 4.03 mmol) and the mixture are stirred for 30 minutes. The reaction is quenched with water (0.5 mL), then NaOH (5N, 3.0 mL) and stirred for 10 minutes. The organic layer is concentrated and loaded on column and purified with EtOAc/Hexanes (50%) to obtain the title compound (653 mg, 100%).

Workup

  1. customThe reaction is quenched with water (0.5 mL)
  2. stirringNaOH (5N, 3.0 mL) and stirred for 10 minutes
  3. concentrationThe organic layer is concentrated and loaded on column
  4. custompurified with EtOAc/Hexanes (50%)

Sources & evidence

ORD record
ord-ce4c45ba8da242d299d47f97648ae4d6
Source dataset
uspto-grants-2009_08
Patent number
US07579488B2

Reaction notes

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