Imidazole → tert-Butyldimethyl((4-nitrobenzyl)oxy)silane

HRID 33985

반응식

HRID 33985 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[N+:14]([C:17]1[CH:24]=[CH:23][C:20]([CH2:21][OH:22])=[CH:19][CH:18]=1)([O-:16])=[O:15]>CN(C=O)C.O>[C:4]([Si:1]([CH3:3])([CH3:2])[O:22][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([N+:14]([O-:16])=[O:15])=[CH:24][CH:23]=1)([CH3:7])([CH3:6])[CH3:5]

참가 물질

6

반응물 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 692754-Nitrobenzyl alcohol

생성물 1

HCID 11065418tert-Butyldimethyl((4-nitrobenzyl)oxy)silane

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A solution of t-butyldimethylsilyl chloride (8.53 g, 56.3 mmol, 1.3 eq), imidazole (7.38 g, 108.3 mmol, 2.5 eq) and 4-nitro-benzyl alcohol (6.64 g, 43.3 mmol, 1 eq) in anhydrous DMF (25 mL) was stirred at room temperature under a N2 atmosphere for 72 h. The reaction mixture was diluted with H2O (500 mL) and extracted with Etoac (4×100 mL). The combined organic extracts were washed with H2O (100 mL), satd NaCl(aq) (100 mL), dried (MgSO4) and evaporated in vacuo. The residue was triturated with n-hexane and filtered. The filtrate was evaporated in vacuo to give the product as a yellow oil which crystallised (11.02 g, 95%). 1H NMR (CDCl3) δ 8.2 (d, J=8.25 Hz, 2H), 7.47 (d, J=8.02 Hz, 2H), 4.8 (s, 2H), 0.96 (s, 9H), 0.12 (s, 6H). IR (neat) 2955, 2930, 1605 and 1522 cm−1. HRMS m/z calcd for C13H22NO3 Si 268.1369 (M+H), found 268.1376

후처리

  1. extractionextracted with Etoac (4×100 mL)
  2. washThe combined organic extracts were washed with H2O (100 mL), satd NaCl(aq) (100 mL)
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was triturated with n-hexane
  6. filtrationfiltered
  7. customThe filtrate was evaporated in vacuo

출처 및 근거

ORD 기록
ord-5d60c1b5bbc1400f94b655657d222ae0
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429658B2

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