Hydrochloric Acid → HCID 59714853, compound

HRID 2223867Notes

Reaction equation

HRID 2223867 reaction equation
[C:1]([O:4][CH2:5][C:6]([CH2:18][CH2:19][C:20]1([CH2:26][CH2:27][O:28][Si](C(C)(C)C)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)([CH2:12][CH2:13][O:14][C:15](=[O:17])[CH3:16])[CH2:7][O:8][C:9](=[O:11])[CH3:10])(=[O:3])[CH3:2].Cl.O>CO.O1CCCC1>[C:9]([O:8][CH2:7][C:6]([CH2:18][CH2:19][C:20]1([CH2:26][CH2:27][OH:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)([CH2:12][CH2:13][O:14][C:15](=[O:17])[CH3:16])[CH2:5][O:4][C:1](=[O:3])[CH3:2])(=[O:11])[CH3:10]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 59714905HCID 59714905, compound

Product 1

HCID 59714853HCID 59714853, compoundYield 51.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(acetoxymethyl)-2-[2-[1-[2-(tert-butyldiphenylsiloxy)ethyl]cyclohexyl]ethyl]-1,4-diacetoxybutane (340 mg) in methanol (5 mL) and tetrahydrofuran (3 mL) was added 3N hydrochloric acid (2.0 mL) at room temperature. After stirring the solution at room temperature for 5.5 hours, water was added thereto. The solution was concentrated under reduced pressure to distill off methanol and tetrahydrofuran, and it was extracted with ethyl acetate. The organic layer was washed in turn with water and saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then, concentrated under reduced pressure. The resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=4:6) to give the title compound (110 mg).

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. distillationto distill off methanol and tetrahydrofuran, and it
  3. extractionwas extracted with ethyl acetate
  4. washThe organic layer was washed in turn with water and saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by column chromatography (silica gel, hexane:ethyl acetate=4:6)

Sources & evidence

ORD record
ord-0eff1b9bac07436fa6e1eded40416c3f
Source dataset
uspto-grants-2008_05
Patent number
US07375115B2

Reaction notes

Loading…