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

HRID 348732Notes

Reaction equation

HRID 348732 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-4bb6032d1e7d427c89924089d62dcd73
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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