Water → HCID 69554256, compound

HRID 1610256Notes

Reaction equation

HRID 1610256 reaction equation
C([Si]([O:8][CH2:9][C:10]1[C:15]2[CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:14]=2[CH:13]=[CH:12][CH:11]=1)(C)C)(C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>O1CCCC1>[C:10]1([CH2:9][OH:8])[C:15]2[CH:16]=[CH:17][CH2:18][CH2:19][CH2:20][CH2:21][C:14]=2[CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 69553847HCID 69553847, compound

Product 1

HCID 69554256HCID 69554256, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of tert-butyl(5,6,7,8-tetrahydrobenzo[a]cycloocten-1-ylmethoxy)dimethylsilane (10.94 g, 36.16 mmol) in tetrahydrofuran (100 ml) was added a solution (43.4 ml, 43.4 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=6/1−3/1) 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=6/1−3/1)
  6. customto give the objective substance

Sources & evidence

ORD record
ord-d392ac3de762464ab2a161d82c913097
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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