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Triethylamine → 2-t-Butyl-5-[(1E)-3-(t-butyldimethylsilyloxy)propenyl]-1-nitrobenzene

HRID 1418183
ノート
印刷プレビュー

反応式

HRID 1418183 の反応式
[C:1]([SiH:5]([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.[C:15]([C:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH2:27][OH:28])=[CH:21][C:20]=1[N+:29]([O-:31])=[O:30])([CH3:18])([CH3:17])[CH3:16]>CN(C)C1C=CN=CC=1.CN(C)C=O>[C:15]([C:19]1[CH:24]=[CH:23][C:22](/[CH:25]=[CH:26]/[CH2:27][O:28][Si:5]([C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:7])[CH3:6])=[CH:21][C:20]=1[N+:29]([O-:31])=[O:30])([CH3:18])([CH3:16])[CH3:17]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 8471TriethylamineHCID 5072427tert-ButyldimethylsilaneHCID 193484672-t-Butyl-5-[(1E)-3-hydroxy-1-propenyl]-1-nitrobenzene

生成物 1

HCID 193487852-t-Butyl-5-[(1E)-3-(t-butyldimethylsilyloxy)propenyl]-1-nitrobenzene収率 96.9%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒
HCID 6228
Dimethylformamide
溶媒

実験手順

11.6 g (77 mmol) of t-butyldimethylsilane, 7.8 g (77 mmol) of triethylamine and 0.76 g (6.2 mmol) of 4-dimethylaminopyridine were added, in turn, and with ice-cooling, to a solution of 14.5 g (62 mmol) of 2-t-butyl-5-[(1E)-3-hydroxy-1-propenyl]-1-nitrobenzene [prepared as described in step (iii) above] in 140 ml of dimethylformamide, and the resulting mixture was stirred for 1 hour. At the end of this time, the reaction mixture was poured into ice-water and then extracted with diethyl ether. The extract was washed with a 10% w/w aqueous solution of hydrochloric acid, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order, after which it was dried. The solvent was then removed by distillation under reduced pressure, and the resulting residue was purified by column chromatography through silica gel, using a 1:15 by volume mixture of ethyl acetate and hexane, to give 21 g of the title compound as crystals, melting at 33°-34° C. (from ethyl acetate-hexane).

後処理

  1. extractionextracted with diethyl ether
  2. washThe extract was washed with a 10% w/w aqueous solution of hydrochloric acid, with a saturated aqueous solution of sodium hydrogencarbonate and with a saturated aqueous solution of sodium chloride, in that order
  3. customafter which it was dried
  4. customThe solvent was then removed by distillation under reduced pressure
  5. customthe resulting residue was purified by column chromatography through silica gel
  6. additionby volume mixture of ethyl acetate and hexane

出典と根拠

ORDレコード
ord-f0caa0ca30c6406683a900ed4b151fe9
出典データセット
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05880147

反応ノート

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