Triethylamine → 3-(t-Butyldimethylsilyloxymethyl)phenyl 2-(acetyloxy)benzoate

HRID 1862537Notes

Reaction equation

HRID 1862537 reaction equation
[Si:1]([O:8][CH2:9][C:10]1[CH:11]=[C:12]([OH:16])[CH:13]=[CH:14][CH:15]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[C:17]([O:20][C:21]1[C:22](=[CH:26][CH:27]=[CH:28][CH:29]=1)[C:23](Cl)=[O:24])(=[O:19])[CH3:18].C(N(CC)CC)C>CCOCC.CCOC(C)=O>[C:17]([O:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([O:16][C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[CH:11]=1)=[O:24])(=[O:19])[CH3:18]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 796682-Acetoxybenzoyl chloride2×HCID 149405563-((((1,1-Dimethylethyl)dimethylsilyl)oxy)methyl)phenol

Product 1

HCID 120710543-(t-Butyldimethylsilyloxymethyl)phenyl 2-(acetyloxy)benzoateYield 100%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Compound 3 in Et2O (120 ml) were added acetylsalicyloyl chloride (Compound 4) (5.9 g, 0.028 mol) and triethylamine (Et3N) (6.6 ml, 0.047 mol) in sequence at RT. The reaction mixture was stirred at RT under argon for 3 days. The reaction mixture was diluted with EtOAc (100 ml) and washed with aqueous saturated NaHCO3 (3×100 ml), brine (1×100 ml), and dried over anhydrous Na2SO4. The crude product obtained upon concentration was purified by column chromatography (elution solvent: 5% EtOAc in hexanes) to produce 9.4 g of Compound 5 in 100% yield.

Workup

  1. washwashed with aqueous saturated NaHCO3 (3×100 ml), brine (1×100 ml)
  2. dry with materialdried over anhydrous Na2SO4
  3. customThe crude product obtained upon concentration
  4. customwas purified by column chromatography (elution solvent: 5% EtOAc in hexanes)

Sources & evidence

ORD record
ord-e698fe58e16d4fa2a1f2009aa22ff3b1
Source dataset
uspto-grants-2003_03
Patent number
US06538033B2

Reaction notes

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