Hydrochloric Acid → HCID 59714919, compound

HRID 2223855Notes

Reaction equation

HRID 2223855 reaction equation
[O:1]([CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][C:29]([C:40]([O:42][CH2:43][CH3:44])=[O:41])([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:30]([O:32][CH2:33][CH3:34])=[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.O1CCCC1.Cl.O>CO>[OH:1][CH2:19][CH2:20][C:21]1([CH2:27][CH2:28][C:29]([C:30]([O:32][CH2:33][CH3:34])=[O:31])([C:40]([O:42][CH2:43][CH3:44])=[O:41])[C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:22][CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 59714892HCID 59714892, compound

Product 1

HCID 59714919HCID 59714919, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of triethyl 3-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]-1,1,1-propanetricarboxylate (470 mg) in methanol (10 mL)/tetrahydrofuran (5 mL) was added 3N hydrochloric acid (2.5 mL) at room temperature. After stirring the solution at room temperature for 4 hours, water was added to the solution, and it was concentrated under reduced pressure. The solution was extracted with ethyl acetate. The organic layer was washed in turn with water and saturated aqueous sodium chloride solution. The solution was 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 (230 mg).

Workup

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

Sources & evidence

ORD record
ord-6eddd9bf29a34012b39ba7acf0e5ec5e
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

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