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

HRID 348735
Notes
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Reaction equation

HRID 348735 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-e6fe9df5ce3449bebf2a11a3b6d20ed7
Source dataset
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07176227B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes