Ammonium Chloride → 2-t-Butyldimethylsilyloxymethyl-6-hydroxymethylnaphthalene

HRID 1173985Notes

Reaction equation

HRID 1173985 reaction equation
[OH:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][OH:14])[CH:9]=2)[CH:4]=1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].[Cl-].[NH4+]>CN(C=O)C.N1C=CN=C1>[Si:15]([O:1][CH2:2][C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([CH2:13][OH:14])[CH:9]=2)[CH:4]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 117887222,6-Bis(hydroxymethyl)naphthalene

Product 1

HCID 230792982-t-Butyldimethylsilyloxymethyl-6-hydroxymethylnaphthaleneYield 48.9%

Reagents, catalysts & solvents 2

HCID 795ImidazoleSolventHCID 6228DimethylformamideSolvent2×

Procedure

The compound (3.41 g) obtained in Example 121-1 was dissolved in anhydrous DMF (200 ml). Then, t-butyldimethylsilyl chloride (2.73 g) dissolved in imidazole (1.48 g) and anhydrous DMF (50 ml) was dropped in this solution, and the whole was stirred overnight at room temperature. After completion of the reaction, the solution was added with a saturated aqueous ammonium chloride solution and stirred. The solution was extracted with chloroform and the extract was then washed with a saturated aqueous sodium bicarbonate solution, a saturated aqueous ammonium chloride solution, and saturated saline solution. Then, the organic layer was dried with anhydrous sodium sulfate. Subsequently, the solvent was distilled off and the residue was then purified through silica gel column chromatography (chloroform), thereby obtaining the subject compound (2.68 g) as a white solid.

Workup

  1. customAfter completion of the reaction
  2. stirringstirred
  3. extractionThe solution was extracted with chloroform
  4. washthe extract was then washed with a saturated aqueous sodium bicarbonate solution
  5. dry with materialThen, the organic layer was dried with anhydrous sodium sulfate
  6. distillationSubsequently, the solvent was distilled off
  7. customthe residue was then purified through silica gel column chromatography (chloroform)

Sources & evidence

ORD record
ord-e0ca2bb8943841e482b7cbdd50e9ed07
Source dataset
uspto-grants-2010_11
Patent number
US07833991B2

Reaction notes

Loading…