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

HRID 33985

反応式

HRID 33985 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-5d60c1b5bbc1400f94b655657d222ae0
出典データセット
uspto-grants-2008_09
特許番号
US07429658B2

関連ノート

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