Methyl 3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzoate → 3-Tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl alcohol

HRID 369821Notes

Reaction equation

HRID 369821 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:18])[CH3:17])[C:8](OC)=[O:9])([CH3:4])([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1>C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[CH:13][C:14]=1[O:15][Si:16]([C:19]([CH3:22])([CH3:21])[CH3:20])([CH3:17])[CH3:18])[CH2:8][OH:9])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 18352492Methyl 3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzoateHCID 86583787Diisobutylaluminumhydride toluene2×

Product 1

HCID 539541643-Tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl alcoholYield 90%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

According to example 184, 5.00 g of methyl 3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzoate was reduced using 31.8 mL of 1M diisobutylaluminum hydride/toluene and 50 mL of anhydrous toluene. Analysis of the reaction mixture by tlc after 30 min indicated some remaining starting material. To ensure complete reduction, an additional 5 mL of 1M diisobutylaluminum hydride/toluene was added and the reaction was allowed to proceed for an additional 5 min. Work-up in the usual manner afforded 4.11 g (90%) of 3-tert-butyl-4-((tert-butyldimethylsilyl)oxy)benzyl alcohol as a cloudy oil. The product was used without further purification.

Workup

  1. waitto proceed for an additional 5 min

Sources & evidence

ORD record
ord-c3b729b626ff4c30aff16de73400e83d
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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