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

HRID 257833

Reaction equation

HRID 257833 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-aed1f222c793456188b036b61c3b73f5
Source dataset
uspto-grants-1993_11
Patent number
US05264439

Linked notes

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