Aluminium lithium hydride → [4-(1-{4-[2-(t-Butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylphenyl]methanol

HRID 502057Notes

Reaction equation

HRID 502057 reaction equation
[Si:1]([O:8][CH:9]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:23]2[CH:32]=[CH:31][C:26]([C:27](OC)=[O:28])=[C:25]([CH3:33])[CH:24]=2)([CH2:21][CH3:22])[CH2:19][CH3:20])=[CH:14][C:13]=1[CH3:34])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[Si:1]([O:8][CH:9]([C:35]([CH3:36])([CH3:37])[CH3:38])[CH2:10][O:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]([C:23]2[CH:32]=[CH:31][C:26]([CH2:27][OH:28])=[C:25]([CH3:33])[CH:24]=2)([CH2:19][CH3:20])[CH2:21][CH3:22])=[CH:14][C:13]=1[CH3:34])([C:4]([CH3:5])([CH3:7])[CH3:6])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57763479Methyl 4-(1-{4-[2-(t-butyldimethylsilanyloxy)-3,3-dimethyl-butoxy]-3-methylphenyl}-1-ethylpropyl)-2-methyl-benzoate

Product 1

HCID 57763514[4-(1-{4-[2-(t-Butyldimethylsilanyloxy)-3,3-dimethylbutoxy]-3-methylphenyl}-1-ethylpropyl)-2-methylphenyl]methanolYield 99.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 0° C. solution of the methyl 4-(1-{4-[2-(t-butyldimethylsilanyloxy)-3,3-dimethyl-butoxy]-3-methylphenyl}-1-ethylpropyl)-2-methyl-benzoate (4.37 g, 8.09 mmol) in THF (50 mL) is added LiAlH4 (0.31 g, 8.09 mmol). The reaction is stirred for 10 m and allowed to warm to RT overnight. The mixture is cooled to 0° C. and quenched successively with H2O (0.3 mL), 15% NaOH (0.3 mL) and H2O (0.9 mL). The mixture is stirred for 10 m, warmed to RT, stirred for 20 m, filtered through celite with EtOAc (100 mL) wash, and concentrated to give the title compound (4.14 g, 8.08 mmol, 99%).

Workup

  1. temperatureThe mixture is cooled to 0° C.
  2. customquenched successively with H2O (0.3 mL), 15% NaOH (0.3 mL) and H2O (0.9 mL)
  3. stirringThe mixture is stirred for 10 m
  4. temperaturewarmed to RT
  5. stirringstirred for 20 m
  6. filtrationfiltered through celite with EtOAc (100 mL)
  7. washwash
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-0c14f63de5394c69b53446d5621800b0
Source dataset
uspto-grants-2010_08
Patent number
US07772425B2

Reaction notes

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