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

HRID 1418183
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HRID 1418183 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매
HCID 6228
Dimethylformamide
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-f0caa0ca30c6406683a900ed4b151fe9
출처 데이터셋
uspto-grants-1999_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05880147

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