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

HRID 6520
ノート
印刷プレビュー

反応式

HRID 6520 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6342
Acetonitrile
溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-5ce452de6da847909012d9a70df1b395
出典データセット
uspto-grants-1993_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05248830

反応ノート

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