Methanol → 3-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propan-1-ol

HRID 1173988Notes

Reaction equation

HRID 1173988 reaction equation
C[O:2][C:3](=O)[CH2:4][CH2:5][C:6]1[CH:15]=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH2:16][O:17][Si:18]([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19])[CH:12]=2)[CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.C(C(C(C([O-])=O)O)O)([O-])=O.[Na+].[K+]>C1COCC1>[Si:18]([O:17][CH2:16][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[CH:7]=[C:6]([CH2:5][CH2:4][CH2:3][OH:2])[CH:15]=[CH:14]2)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 887MethanolHCID 9855836Potassium sodium tartarateHCID 21226445Aluminium lithium hydrideHCID 669415313-(6-t-butyldimethylsilyloxymethylnaphthalen-2-yl)propionic Acid Methyl Ester

Product 1

HCID 230791693-(6-t-Butyldimethylsilyloxymethylnaphthalen-2-yl)propan-1-olYield 109.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound (2.62 g) obtained in Example 121-5 was dissolved in anhydrous THF (100 ml) and added with lithium aluminum hydride (555 mg) under ice-cooling, followed by stirring for 30 minutes under a nitrogen atmosphere. After completion of the reaction, the solution was added with methanol and then added with an aqueous potassium sodium tartrate solution, followed by stirring overnight. The solution was extracted with chloroform and the extract was washed with saturate saline solution. Then, the organic layer was dried with anhydrous sodium sulfate. The solvent was distilled off, thereby obtaining the subject compound (2.64 g) as a white solid.

Workup

  1. temperaturecooling
  2. customAfter completion of the reaction
  3. stirringby stirring overnight
  4. extractionThe solution was extracted with chloroform
  5. washthe extract was washed
  6. concentrationwith saturate saline solution
  7. dry with materialThen, the organic layer was dried with anhydrous sodium sulfate
  8. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-c17d92a3f1844dca8f23690e37d9cd27
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

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