Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoate → 4-(Tert-butyldimethylsilyloxy)3-(2-propen-1-yl)benzyl alcohol

HRID 1492591Notes

Reaction equation

HRID 1492591 reaction equation
[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([C:13](OC)=[O:14])=[CH:11][C:10]=1[CH2:19][CH:20]=[CH2:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Si:1]([O:8][C:9]1[CH:18]=[CH:17][C:12]([CH2:13][OH:14])=[CH:11][C:10]=1[CH2:19][CH:20]=[CH2:21])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 19385705Methyl 4-(t-butyldimethylsilyloxy)-3-(2-propen-1-yl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 544131774-(Tert-butyldimethylsilyloxy)3-(2-propen-1-yl)benzyl alcoholYield 93.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a magnetically stirred solution of 8.523 g (28.0 mmol) of the product from Step C in 35 mL of anhydrous THF was added 15.0 mL of a 1.0M solution of lithium aluminum hydride in THF, and the reaction mixture was stirred under a nitrogen atmosphere for 2 hours. At this point, the reaction was quenched by cautious addition of 10 mL water, the resulting precipitate was dissolved by addition of 1.0N hydrochloric acid and the product was extracted into ethyl acetate. The organic layer was separated, dried (MgSO4), filtered and evaporated in vacuo to afford 7.258 g (93%) of the title compound.

Workup

  1. customAt this point, the reaction was quenched by cautious addition of 10 mL water
  2. dissolutionthe resulting precipitate was dissolved by addition of 1.0N hydrochloric acid
  3. extractionthe product was extracted into ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-ce7b648869e948be9e69237863890ad0
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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