Water → 3,5-Bis(trifluoromethyl)-alpha-{[2-(trimethylsilyl)ethoxy]methoxymethyl}benzenemethanol

HRID 966967ノート

反応式

HRID 966967 の反応式
C(N(C(C)C)C(C)C)C.[F:10][C:11]([F:27])([F:26])[C:12]1[CH:13]=[C:14]([CH:22]([OH:25])[CH2:23][OH:24])[CH:15]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:17]=1.Cl[CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34].O>ClCCl>[F:10][C:11]([F:26])([F:27])[C:12]1[CH:13]=[C:14]([CH:22]([CH2:23][O:24][CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[OH:25])[CH:15]=[C:16]([C:18]([F:20])([F:21])[F:19])[CH:17]=1

参加物

6

反応物 4

HCID 962WaterHCID 81531DiisopropylethylamineHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 222935121-[3,5-Bis(trifluoromethyl)phenyl]ethane-1,2-diol

生成物 1

HCID 865903613,5-Bis(trifluoromethyl)-alpha-{[2-(trimethylsilyl)ethoxy]methoxymethyl}benzenemethanol収率 49%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

N-Ethyl-N,N-diisopropylamine (465 μl, 2.67 mmol) was added over 2 minutes, to a solution of (RS)-1-[3,5-bis(trifluoromethyl)phenyl]-1,2-ethanediol (Description 3, 488 mg, 1.78 mmol) and [2-(chloromethoxy)ethyl]trimethylsilane (315 μl, 1.78 mmol) in dichloromethane (3 mL) and the mixture was stirred at room temperature for 4 hours, then at 50° C. for 1 hour. The mixture was cooled and dichloromethane (20 mL) and water (20 mL) were added. The layers were separated and the aqueous layer was extracted with dichloromethane (10 mL). The combined organic fractions were dried (Na2SO4) and the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography on silica gel, eluting with isohexane/EtOAc (90:10) to give the title compound (352 mg, 49%). 1H NMR (400 MHz, CDCl3) δ 7.86 (2H, s), 7.79 (1H, s), 4.96 (1H, m), 4.73 (2H, s), 3.87 (1H, dd, J 11.1, 3.0 Hz), 3.73 (1H, br s), 3.61 (3H, m), 0.93 (2H, t, J 8.5 Hz), and 0.02 (9H, s).

後処理

  1. waitat 50° C. for 1 hour
  2. temperatureThe mixture was cooled
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with dichloromethane (10 mL)
  5. dry with materialThe combined organic fractions were dried (Na2SO4)
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by flash column chromatography on silica gel
  8. washeluting with isohexane/EtOAc (90:10)

出典と根拠

ORDレコード
ord-26ef180a91d445458ac6694f42f4c006
出典データセット
uspto-grants-2005_10
特許番号
US06953792B2

反応ノート

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