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

HRID 1862537

반응식

HRID 1862537 반응식
[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]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 796682-Acetoxybenzoyl chloride2회HCID 149405563-((((1,1-Dimethylethyl)dimethylsilyl)oxy)methyl)phenol

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 8857Ethyl Acetate용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e698fe58e16d4fa2a1f2009aa22ff3b1
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06538033B2

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