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

HRID 1862537ノート

反応式

HRID 1862537 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-e698fe58e16d4fa2a1f2009aa22ff3b1
出典データセット
uspto-grants-2003_03
特許番号
US06538033B2

反応ノート

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