Sodium Hydroxide → HCID 19348623, compound

HRID 1418198Notes

Reaction equation

HRID 1418198 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[C:12]([O:20][CH3:21])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O>[Si:1]([O:8][CH2:9][C:10]1[CH:19]=[CH:18][C:13]([CH2:14][OH:15])=[C:12]([O:20][CH3:21])[CH:11]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 19348729HCID 19348729, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 19348623HCID 19348623, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 32.19 g (0.101 mol) of methyl 4-(t-butyldimethylsilyl-oxymethyl)-2-methoxybenzoate (prepared as described in Preparation 39) in 50 ml of tetrahydrofuran was added dropwise to an ice-cooled suspension of 3.51 g (92.5 mmol) of lithium aluminum hydride in 250 ml of tetrahydrofuran over a period of 30 minutes. The resulting mixture was then stirred at the same temperature for 1 hour and then at room temperature for 40 minutes. At the end of this time, the reaction mixture was again cooled with ice, and 3.5 ml of water were added to the mixture to terminate the reaction. 3.5 ml of a 15% w/v aqueous solution of sodium hydroxide and 10.5 ml of water were then added, with stirring, to the mixture. Anhydrous magnesium sulfate was added, and the reaction mixture was filtered. The filtrate was freed from the solvent by distillation under reduced pressure, to give 29.30 g (a quantitative yield) of the title compound.

Workup

  1. temperaturecooled
  2. waitat room temperature for 40 minutes
  3. additionwere added to the mixture
  4. customto terminate
  5. customthe reaction
  6. stirringwith stirring, to the mixture
  7. filtrationthe reaction mixture was filtered
  8. distillationThe filtrate was freed from the solvent by distillation under reduced pressure

Sources & evidence

ORD record
ord-1a9767e81d204c0c900925667fe059f6
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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