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

HRID 964743

반응식

HRID 964743 반응식
[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]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 692754-Nitrobenzyl alcoholHCID 94078tert-Butyldiphenylchlorosilane

생성물 1

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

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

To a stirred solution of 4-nitrobenzyl alcohol, 12, (1.00 g, 6.50 mmol), and imidazole (0.97 g, 14.1 mmol) in DMF (10.0 ml), was added tert-butyl-diphenyl-chlorosilane (1.98 g, 7.20 mmol) over 10 min under N2 at room temperature. The reaction mixture was stirred for an additional 5 h, diluted with Et2O (75 ml), washed with H2O (5×15 ml), dried (MgSO4) and evaporated to dryness under vacuum. An oil was obtained which crystallised on standing and was recrystallised to a solid from EtOH (70%); yield: 2.36 g (93%). vmax /cm-1 (film): 2931, 2857 (CH2, asym., sym.), 1521, 1345 (NO2); 1H-NMR, dH : 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, 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.

후처리

  1. washwashed with H2O (5×15 ml)
  2. dry with materialdried (MgSO4)
  3. customevaporated to dryness under vacuum
  4. customAn oil was obtained which
  5. customcrystallised
  6. customwas recrystallised to a solid from EtOH (70%)

출처 및 근거

ORD 기록
ord-a044b80c49bf4e618e7b4e946b26ea5c
출처 데이터셋
uspto-grants-1998_06
특허 번호
US05770731

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