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

HRID 348732
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HRID 348732 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 795Imidazole용매
HCID 6228
Dimethylformamide
용매
2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-4bb6032d1e7d427c89924089d62dcd73
출처 데이터셋
uspto-grants-2007_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07176227B2

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