Imidazole → 2-[2-(t-Butyldimethylsiloxy)ethyl]phenol

HRID 327351

反応式

HRID 327351 の反応式
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10].[Si:11](Cl)([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12].N1C=CN=C1.CCOC(C)=O>CN(C=O)C>[O:1]([CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[OH:10])[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12]

参加物

6

反応物 4

HCID 795ImidazoleHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 822002-(2-Hydroxyethyl)phenol

生成物 1

HCID 149405572-[2-(t-Butyldimethylsiloxy)ethyl]phenol

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Hydroxyethylphenol (XLVa) (15.2 g, 0.11 mol) and t-butyldimethylsilyl chloride (18.2 g, 0.121 mol) were placed together in DMF (120 mL; Aldrich Sure Seal). While the solution was being stirred, imidazole (16.5 g, 0.242 mol) was added portionwise (slightly exothermic). After stirring for 3 h at room temperature, EtOAc (200 mL) was added and the resultant solution was washed with water (3×200 mL) and brine (200 mL). The EtOAc layer was dried over anhydrous sodium sulfate, filtered and concentrated to leave a yellow oil which was purified by silica gel column chromatography (being eluted with 19:1 hexanes/EtOAc) to obtain 27.7 g (0.11 mol, Y: 100%) of the title compound as an oil; Rf: 0.40 (19:1 hexanes/EtOAc); 1H-NMR (CDCl3) δ ppm: 0.067 (6H, s, SiMe2), 0.893(9H, s, SitBu), 2.87 (2H, t, J=5 Hz, ArCH2), 3.91 (2H, t, J=5 Hz, CH2OSi), 6.80 (1H, dt, J=1.3, 7.4 Hz, 5'-H), 6.90 (1H, dd, J=1.2, 8 Hz, 2'-H), 7.00 (1H, dd, J=1,5, 7.3 Hz, 6'-H), 7.12 (1H, dt, J=1.6, 7.5 Hz, 4'-H), 8.29 (1H, s, OH, D2O exchanged); IR (film) 3300 (OH), 1616 cm-1 ; MS (FAB/NOBA) m/e: 253 (MH+), 237, 209.

後処理

  1. stirringAfter stirring for 3 h at room temperature
  2. washthe resultant solution was washed with water (3×200 mL) and brine (200 mL)
  3. dry with materialThe EtOAc layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto leave a yellow oil which
  7. customwas purified by silica gel column chromatography (being eluted with 19:1 hexanes/EtOAc)

出典と根拠

ORDレコード
ord-62e5732a9ff446658f12155889331289
出典データセット
uspto-grants-1993_12
特許番号
US05272171

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