HCID 19385687, compound → (4-{[tert-Butyl(dimethyl)silyl]oxy}-3-chlorophenyl)methanol

HRID 1492574Notes

Reaction equation

HRID 1492574 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[Cl:19])([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[Cl:19])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 19385687HCID 19385687, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 54570390(4-{[tert-Butyl(dimethyl)silyl]oxy}-3-chlorophenyl)methanolYield 54.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred and cooled (0° C.) solution of 8.00 g (26.7 mmol) of the product of Step A dissolved in 50 mL of anhydrous THF was added 53.3 mL (53.3 mmol) of a 1M solution of lithium aluminum hydride in THF. After the addition was complete the reaction mixture was allowed to warm to room temperature and stirred 2 hours. The stirred reaction was then quenched by dropwise addition of 2.5 mL water, then 2.5 mL of 15% NaOH, and finally 7.5 mL water. The reaction mixture was then filtered and concentrated in vacuo. The residue was dissolved in ethyl acetate, washed with 1N HCl, saturated NaHCO3, dried (MgSO4), and evaporated in vacuo to afford 4.0 g (53%) of the title compound.

Workup

  1. additionAfter the addition
  2. stirringstirred 2 hours
  3. customThe stirred reaction
  4. customwas then quenched by dropwise addition of 2.5 mL water
  5. filtrationThe reaction mixture was then filtered
  6. concentrationconcentrated in vacuo
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washwashed with 1N HCl, saturated NaHCO3
  9. dry with materialdried (MgSO4)
  10. customevaporated in vacuo

Sources & evidence

ORD record
ord-a5530d0a929e441893bf8573df618ba9
Source dataset
uspto-grants-1994_12
Patent number
US05374638

Reaction notes

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