Ammonium Chloride → HCID 57683257, compound

HRID 1864963Notes

Reaction equation

HRID 1864963 reaction equation
[F:1][C:2]([F:21])([F:20])[CH2:3][NH:4][C:5]([CH:7]1[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6].C([N-]C(C)C)(C)C.[Li+].[Si:30]([O:37][CH2:38][CH2:39]Br)([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31].[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]([F:20])([F:21])[CH2:3][NH:4][C:5]([C:7]1([CH2:39][CH2:38][O:37][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:13]2[C:8]1=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:6]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 2724682Lithium diisopropylamideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 17916968HCID 17916968, compound

Product 1

HCID 57683257HCID 57683257, compoundYield 129.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

9H-Fluorene-9-carboxylic acid (2,2,2-trifluoroethyl)amide (3.00 g) was dissolved in tetrahydrofuran (100 mL), and to this solution was added dropwise a 1.5M solution (13.7 mL) of lithium diisopropylamide under ice-cooling. The mixture was stirred for one hour under ice-cooling, and to this was added a solution of tert-butyldimethylsilanyloxyethyl bromide (2.46 g) in tetrahydrofuran (5 mL). The temperature was gradually raised from under ice-cooling to room temperature, and the mixture was stirred overnight. Saturated aqueous ammonium chloride was added to the reaction mixture under ice-cooling and then extracted with ethyl acetate (50 mL×2). The extract was washed with saturated brine, dried over sodium sulfate and purified by column chromatography on silica gel with ethyl acetate:hexane=1:2.5 to give the title compound (6.00 g).

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. temperatureThe temperature was gradually raised from under ice-
  4. stirringthe mixture was stirred overnight
  5. temperaturecooling
  6. extractionextracted with ethyl acetate (50 mL×2)
  7. washThe extract was washed with saturated brine
  8. dry with materialdried over sodium sulfate
  9. custompurified by column chromatography on silica gel with ethyl acetate

Sources & evidence

ORD record
ord-0babf854bd0e4046b299da55fcbfddad
Source dataset
uspto-grants-2009_12
Patent number
US07625948B2

Reaction notes

Loading…