Ammonia → (3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanol

HRID 505677

Reaction equation

HRID 505677 reaction equation
[C:1]1([CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][OH:8])[CH:2]=1.C(N(CC)CC)C.[C:18]([Si:22]([CH3:25])([CH3:24])Cl)([CH3:21])([CH3:20])[CH3:19].N>ClCCl>[Si:22]([O:8][CH2:7][C:3]1[CH:2]=[C:1]([CH2:9][OH:10])[CH:6]=[CH:5][CH:4]=1)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:25])[CH3:24]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 693741,3-Benzenedimethanol

Product 1

HCID 10658493(3-((Tert-butyldimethylsilyloxy)methyl)phenyl)methanolYield 45.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1,3-benzenedimethanol (5.10 g, 36.91 mmol) in dichloromethane (70 ml) was added at 0° C. triethylamine (7.47 g, 73.82 mmol), 4-dimethyl-aminopyridine (451 mg, 3.61 mmol) and t-butyldimethylchlorosilane (5.56 g, 36.91 mmol) successively, and the mixture was stirred for 20 hours at room temperature. Thereto was added a saturated ammonia solution and the mixture was extracted with ethyl acetate and separated by a separating funnel. The organic layer was washed with water and saturated brine, dried over magnesium sulfate and filtered. The solvent was removed in vacuo and the residue was purified by silica gel column chromatography to give the subject compound (4.23 g, 45%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. customseparated by a separating funnel
  3. washThe organic layer was washed with water and saturated brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customThe solvent was removed in vacuo
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-50fc8bbb3b3b47048f33b51ad57a2c25
Source dataset
uspto-grants-2010_08
Patent number
US07781479B2

Linked notes

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