Methanol → HCID 123803795, compound

HRID 549655Notes

Reaction equation

HRID 549655 reaction equation
[C:1]([O:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].N1C=CC=CC=1.OCC1[CH:21]=[CH:20][C:19]([SiH:22]([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=1.CO>C(OCC)(=O)C>[C:5]([O:4][CH2:1][C:2]1[CH:17]=[CH:18][C:19]([SiH:22]([CH:23]([CH3:25])[CH3:24])[CH:26]([CH3:27])[CH3:28])=[CH:20][CH:21]=1)(=[O:7])[CH3:6]

Participants

6

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 7918Acetic AnhydrideHCID 57568187HCID 57568187, compound

Product 1

HCID 123803795HCID 123803795, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Acetic anhydride (3.1 mL, 33 mmol) and 4-N,N-dimethylaminoprydine (7.3 mg, 6 mmol) were added under argon atmosphere to pyridine (100 mL) dissolving 4-(hydroxymethyl)phenyl-diisopropylsilane (3) (4.9 g, 22 mmol). The resulting mixture was then stirred for 2 hours at a room temperature and methanol (20 mL) was added to it. The reaction mixture was diluted with ethyl acetate (400 mL), and then extracted three times with saturated saline solution (300 mL). An organic layer was collected and dehydrated with anhydrous sodium sulfate and filtered so that the resulting solvent was distilled out under a reduced pressure to give a desired product (5.4 g, 93%). Its NMR data are as follows:

Workup

  1. extractionextracted three times with saturated saline solution (300 mL)
  2. customAn organic layer was collected
  3. filtrationfiltered so that the resulting solvent
  4. distillationwas distilled out under a reduced pressure

Sources & evidence

ORD record
ord-b260da287fec4b56b2ceadf672f8e662
Source dataset
uspto-grants-2011_05
Patent number
US07943758B2

Reaction notes

Loading…