HCID 17756279, compound → HCID 17756175, compound

HRID 2382547Notes

Reaction equation

HRID 2382547 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10][CH2:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[C:18]([Si:15]([CH3:17])([CH3:16])[O:14][CH2:13][CH2:12][CH2:11][CH2:10][C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1)([CH3:19])([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 17756279HCID 17756279, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 17756175HCID 17756175, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirring cooled (0° C.) solution of 4-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-benzoic acid methyl ester (0.80 g, 2.48 mol) in THF (5.5 mL) was added dropwise a solution of lithium aluminum hydride (4.96 mL, 1M in THF). After completion of addition the reaction mixture continued to stir at room temperature. After 2 hours, the reaction mixture was quenched with water. The aqueous layer was extracted with ethyl acetate. All combined organic layers were dried over Na2SO4, filtered, and concentrated to yield a yellow oil. The crude material was purified using silica gel chromatography (1:2 ethyl acetate:hexanes) to afford {4-[4-(tert-butyl-dimethyl-silanyloxy)-butyl]-phenyl}-methanol (0.65 g, 2.21 mol, 89% yield).

Workup

  1. additionAfter completion of addition the reaction mixture
  2. customthe reaction mixture was quenched with water
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialwere dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto yield a yellow oil
  8. customThe crude material was purified

Sources & evidence

ORD record
ord-76bfb0bf1e2f445f86a4b340361ddf60
Source dataset
uspto-grants-2012_09
Patent number
US08263042B2

Reaction notes

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