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Methyl N-(triethylammoniosulfonyl)carbamate → 1-((Trimethylsilyl)ethynyl)-2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexene

HRID 6520
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HRID 6520 반응식
[CH3:1][Si:2]([C:5]#[C:6][C:7]1(O)[C:12]([CH3:14])([CH3:13])[CH2:11][C:10]([CH3:16])([CH3:15])[CH2:9][CH:8]1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([CH3:24])[CH:18]=1)([CH3:4])[CH3:3].CC[N+](S(N=C(OC)[O-])(=O)=O)(CC)CC>C(#N)C.O>[CH3:3][Si:2]([C:5]#[C:6][C:7]1[C:12]([CH3:14])([CH3:13])[CH2:11][C:10]([CH3:16])([CH3:15])[CH2:9][C:8]=1[C:17]1[CH:22]=[CH:21][C:20]([F:23])=[C:19]([CH3:24])[CH:18]=1)([CH3:1])[CH3:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 2

HCID 2724994Methyl N-(triethylammoniosulfonyl)carbamateHCID 197938911-((Trimethylsilyl)ethynyl)-2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethyl-cyclohexan-1-ol

생성물 1

HCID 197939071-((Trimethylsilyl)ethynyl)-2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexene수율 67%

시약·촉매·용매 2

HCID 962Water용매HCID 6342
Acetonitrile
용매

실험 절차

To a solution of the hydroxy acetylene from Example 1, Step C above (20 g, 55.5 mmol) in acetonitrile (250 ml) is added 20 g (83 mmol) of Burgess reagent. The reaction mixture is heated at reflux for 14 hours, cooled to room temperature and diluted with H2O (1 L). The aqueous solution is extracted with ether and the combined ether layers are washed with H2O. The ether fraction is dried over MgSO4 and the solvent is removed under reduced pressure. Purification by silica gel chromatography (100% hexane) provides 12.7 g (67%) of 1-((trimethylsilyl)ethynyl)-2-(4-fluoro-3-methylphenyl)-4,4,6,6-tetramethylcyclohexene as an oil: 1H NMR δ=0.0 (s,9), 0.95 (s,6), 1.15 (s,6), 1.4 ((s,2), 2.1 (s,2), 2.2 (s,3), 6.85 (t,1), 7.25 (m,2).

후처리

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for 14 hours
  3. extractionThe aqueous solution is extracted with ether
  4. washthe combined ether layers are washed with H2O
  5. dry with materialThe ether fraction is dried over MgSO4
  6. customthe solvent is removed under reduced pressure
  7. customPurification by silica gel chromatography (100% hexane)

출처 및 근거

ORD 기록
ord-5ce452de6da847909012d9a70df1b395
출처 데이터셋
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05248830

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