Water → HCID 22261700, compound

HRID 1610661Notes

Reaction equation

HRID 1610661 reaction equation
C([Si]([O:8][CH2:9][C:10]1[C:15]2[CH:16]=[CH:17][CH2:18][C:19]([CH3:22])([CH3:21])[CH2:20][C:14]=2[CH:13]=[CH:12][CH:11]=1)(C)C)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[CH3:21][C:19]1([CH3:22])[CH2:18][CH:17]=[CH:16][C:15]2[C:10]([CH2:9][OH:8])=[CH:11][CH:12]=[CH:13][C:14]=2[CH2:20]1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 86593288HCID 86593288, compound

Product 1

HCID 22261700HCID 22261700, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl (6,6-dimethyl-6,7-dihydro-5H-benzo[a]cyclohepten-1-ylmethoxy)dimethylsilane (7.306 g, 23.08 mmol) in tetrahydrofuran (30 ml) was added a solution of 1.0 M tetrabutylammonium fluoride in tetrahydrofuran (27.7 ml, 27.7 mmol) at room temperature, and the mixture was stirred at room temperature for 15 min. The reaction solution was poured into water, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated under reduced pressure. The obtained crude product was purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1) to give the objective substance.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe recovered organic layer was dried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained crude product
  5. customwas purified by silica gel column chromatography (hexane/ethyl acetate=6/1−3/1)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-857abdc23b7b477794441e959411f834
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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