Water → HCID 11558955, compound

HRID 493901Notes

Reaction equation

HRID 493901 reaction equation
[Si:1]([O:8][C@H:9]1[C:15](=[O:16])[C@H:14]2[CH2:17][C@:11]([OH:19])([C:12](=[O:18])[O:13]2)[CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[OH2:20].N1[CH:26]=[CH:25]C=CC=1>C(OC(=O)C)(=O)C.CCCCCC.C(OCC)(=O)C>[C:25]([O:19][C@@:11]12[CH2:17][C@@H:14]([O:13][C:12]1=[O:18])[C:15](=[O:16])[C@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH2:10]2)(=[O:20])[CH3:26]

Participants

6

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 58906148HCID 58906148, compound

Product 1

HCID 11558955HCID 11558955, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 7918Acetic AnhydrideSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

Solution of hydroxy ketone 3 (1.64 g, 5.8 mmol) in anhydrous pyridine (12 mL) and acetic anhydride (5.5 mL) was stirred for 3 h at room temperature. It was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated NaHCO3, saturated CuSO4 and water, dried (MgSO4), and evaporated to give an oily residue which was dissolved in hexane/ethyl acetate (8:2) and filtered through short path of silica gel. Evaporation of solvents gave pure crystalline acetate 4 (1.51 g, 81%). Analytical sample was obtained by recrystallization from hexane/ethyl acetate.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated NaHCO3, saturated CuSO4 and water
  3. dry with materialdried (MgSO4)
  4. customevaporated
  5. customto give an oily residue which
  6. filtrationfiltered through short path of silica gel
  7. customEvaporation of solvents

Sources & evidence

ORD record
ord-6a435020932547d0bff95d1bbf54c313
Source dataset
uspto-grants-2009_05
Patent number
US07538098B2

Reaction notes

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