Imidazole → 9-Methoxymethyl-9-[(tert-butyldimethylsilyl)oxymethyl]-fluorene

HRID 2416162Notes

Reaction equation

HRID 2416162 reaction equation
[CH3:1][O:2][CH2:3][C:4]1([CH2:17][OH:18])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2.N1C=CN=C1.C(N(CC)CC)C.[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>CN(C)C=O.O>[CH3:1][O:2][CH2:3][C:4]1([CH2:17][O:18][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[C:16]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2

Participants

7

Reactant 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 226391039-(Methoxymethyl)-9H-fluorene-9-methanol

Product 1

HCID 226391259-Methoxymethyl-9-[(tert-butyldimethylsilyl)oxymethyl]-fluoreneYield 87.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

1 g of 9-methoxymethyl-9-hydroxymethyl-fluorene (4.2 mmol) was dissolved in 10 ml of N,N-dimethyl formamide, and 0.14 g of imidazole was added thereto. The mixture was cooled in ice-water bath, and 0.87 ml of triethyl amine (6.2 mmol) was added thereto. After stirring for 5 minutes, 0.88 g of tert-butyldimethylsilyl chloride (5.8 mmol) in 10 ml of N,N-dimethyl formamide was added drop-wise, and the mixture was stirred for further 2 hours, followed by stirring at room temperature for 1 hour. The reaction mixture was diluted with 10 ml of water, and extracted twice using 20 ml of dichloromethane for each time. The combined dichloromethane extract was dried over anhydrous sodium sulfate. After filtration, the filtrate was evaporated to give 1.28 g of concentrate (yield 87.6%).

Workup

  1. stirringthe mixture was stirred for further 2 hours
  2. stirringby stirring at room temperature for 1 hour
  3. extractionextracted twice
  4. extractionThe combined dichloromethane extract
  5. dry with materialwas dried over anhydrous sodium sulfate
  6. filtrationAfter filtration
  7. customthe filtrate was evaporated
  8. customto give 1.28 g
  9. concentrationof concentrate (yield 87.6%)

Sources & evidence

ORD record
ord-f0e4dcd6c2f1423f8e9527c7f923011d
Source dataset
uspto-grants-2004_11
Patent number
US06822109B2

Reaction notes

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