HCID 17756279, compound → HCID 17756175, compound

HRID 1723984Notes

Reaction equation

HRID 1723984 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-55b937a2fa524696b3a441a109173870
Source dataset
uspto-grants-2009_02
Patent number
US07485283B2

Reaction notes

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