Imidazole → (4-Nitro-benzyl) t-butyl-di-phenyl-silyl ether

HRID 612812

反応式

HRID 612812 の反応式
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].N1C=CN=C1.[C:17]([Si:21]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)Cl)([CH3:20])([CH3:19])[CH3:18]>CN(C=O)C.CCOCC>[C:17]([Si:21]([O:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1)([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)([CH3:20])([CH3:18])[CH3:19]

参加物

6

反応物 3

HCID 795ImidazoleHCID 692754-Nitrobenzyl alcoholHCID 94078tert-Butyldiphenylchlorosilane

生成物 1

HCID 15528110(4-Nitro-benzyl) t-butyl-di-phenyl-silyl ether

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a stirred solution of 4-nitrobenzyl alcohol (1.00 g, 6.50 mmol) and imidazole (0.97 g, 14.10 mmol) in DMF (10.0 mL), t-butyl-diphenyl-chlorosilane (1.98 g, 1.87 mL, 7.20 mmol) was added over 10 min under nitrogen at room temperature. The reaction mixture was stirred for an additional 5 h, diluted with 75 mL Et2O, washed with H2O (5 times, 15 mL), dried (MgSO4) and evaporated under vacuum. An oil which crystallised on standing, resulted; yield: 2.54 g. After recrystallisation from EtOH 70%, 2.36 g (93%) of a white soiid is obtained mp 80-81° C. νmax /cm-1 (film): 2931. 2857 (CH2, asym., sym.), 1521. 1345 (NO2); 1H-NMR, δH : 1.06(9H, s, t-Bu), 4.92 (2H, s, CH2), 7.42-7.46 (5H, m, Ph), 7.63-7.65 (7H, m, Ph+Harom2+6), 8.23, (2H, d, J=8.23 Hz, Harom3+5); MS, (EI), (391.54); m/z: 334 (M-t-Bu, 100), 288 (M-t-Bu-NO2, 10), 256 (M-t-Bu-Ph, 20), 199 (Ph2SiOH+, 100); C23H25NO3Si.

後処理

  1. washwashed with H2O (5 times, 15 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated under vacuum
  4. customAn oil which crystallised
  5. customresulted
  6. customAfter recrystallisation from EtOH 70%, 2.36 g (93%) of a white soiid
  7. customis obtained mp 80-81° C. νmax /cm-1 (film)

出典と根拠

ORDレコード
ord-ca54813aa4a94c6d958ac93a77406c0d
出典データセット
uspto-grants-1999_12
特許番号
US06005002

関連ノート

読み込み中…