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

HRID 2399507Notes

Reaction equation

HRID 2399507 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 8028TetrahydrofuranSolvent

Procedure

To a magnetically stirred solution of 8.523 g (28.0 mmol) of the product from Step C in 35 mL of anhydrous TBF 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-9a6d766e2d9e4ba0bae66cdd70fb77be
Source dataset
uspto-grants-1995_09
Patent number
US05449682

Reaction notes

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