Water → HCID 23021220, compound

HRID 2223857Notes

Reaction equation

HRID 2223857 reaction equation
[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][CH:29]([C:34]([O:36][CH3:37])=[O:35])[C:30]([O:32][CH3:33])=[O:31])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1.O>O1CCCC1>[OH:1][CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][CH:29]([C:30]([O:32][CH3:33])=[O:31])[C:34]([O:36][CH3:37])=[O:35])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 59714901HCID 59714901, compound

Product 1

HCID 23021220HCID 23021220, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 3-[1-(2-(tert-butyldiphenylsiloxy)ethyl)cyclohexyl]-1,1-propanedicarboxylate (500 mg) in tetrahydrofuran (10 mL) was added a 1M tetrabutylammonium fluoride/tetrahydrofuran solution (1.9 mL) at room teperature. The solution was stirred at room temperature for 3 hours. Water was added to the solution, and it was extracted with ethyl acetate. The organic layer was washed in turn with an aqueous ammonium chloride solution, and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=1:1) to give the title compound (180 mg).

Workup

  1. extractionwas extracted with ethyl acetate
  2. washThe organic layer was washed in turn with an aqueous ammonium chloride solution, and saturated aqueous sodium chloride solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe resulting residue was purified by chromatography (silica gel, hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-d3f95c368e7c4d6ab2d61fe8afc89d6d
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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