Water → HCID 22262013, compound

HRID 1610261Notes

Reaction equation

HRID 1610261 reaction equation
C([Si]([O:8][CH2:9][C:10]1[C:15]2[CH:16]=[C:17]([CH3:21])[CH2:18][CH2:19][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:17]1[CH2:18][CH2:19][CH2:20][C:14]2[CH:13]=[CH:12][CH:11]=[C:10]([CH2:9][OH:8])[C:15]=2[CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 22262198HCID 22262198, compound

Product 1

HCID 22262013HCID 22262013, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl(8-methyl-6,7-dihydro-5H-benzo[a]cyclohepten-1-ylmethoxy)dimethylsilane (5.594 g, 18.49 mmol) in tetrahydrofuran (50 ml) was added a solution (22.2 ml, 22.2 mmol) of 1.0 M tetrabutylammonium fluoride in tetrahydrofuran 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 collected 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) to give the objective substance.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe collected 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)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-a5b2faea3c47466f9587c2a81208543d
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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