Chlorotrimethylsilane → HCID 18357295、化合物

HRID 428345

反応式

HRID 428345 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Li].C[Si](Cl)(C)C.[CH:15]([N:18]([CH:28]([CH3:30])[CH3:29])[C:19](=[O:27])[CH:20]=[CH:21][C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)([CH3:17])[CH3:16]>CSC.C(OCC)C>[CH:28]([N:18]([CH:15]([CH3:17])[CH3:16])[C:19](=[O:27])[CH2:20][CH:21]([C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[C:22]1[S:23][CH:24]=[CH:25][CH:26]=1)([CH3:30])[CH3:29]

参加物

6

反応物 3

HCID 6397ChlorotrimethylsilaneHCID 4444087N,N-Diisopropyl-3-(2-thienyl)propenamideHCID 178506687HCID 178506687、化合物

生成物 1

HCID 18357295HCID 18357295、化合物

試薬・触媒・溶媒 2

HCID 1068Dimethyl Sulfide溶媒HCID 3283Diethyl Ether溶媒2 回

実験手順

Copper(I)bromide dimethyl sulfide complex (4.63 g 22.5 mmol) was dissolved in dimethyl sulfide (18 mL), and diethyl ether (15 mL). The solution was cooled to 0° C., whereafter 2-methoxyphenyllithium (41.2) (45 mmol) was added. After 10 min., the temperature was lowered to −78° C. Trimethylsilylchloride (4.89 g, 45.0 mmol) was added, followed by N,N-diisopropyl-3-(2-thienyl)propenamide (41.1) (3.56 g, 15 mmol) in diethyl ether (20 mL). The temperature was allowed to slowly rise to room temperature overnight. The reaction was quenched with saturated NH4Cl (10 mL) and conc. ammonia (10 mL). Diethyl ether (80 mL) was added and the mixture was filtered through Celite. The aqueous phase was extracted twice with diethyl ether. The combined organic phases were washed once with brine and dried (MgSO4). The solvent was evaporated and the crude product was chromatographed on silica (petroleum ether-ethyl acetate 3:1), affording a yellow oil, 3.75 g (73%): 1H NMR (CDCl3) d 1.12 (t, 6H), 1.29 (t, 6H), 3.02 (m, 2H), 3.4 (br, 1H), 3.80 (s, 3H), 4.03 (m, 1H), 5.26 (t, 1H), 6.8-7.3 (m, 7H).

後処理

  1. additionwas added
  2. customwas lowered to −78° C
  3. waitto slowly rise to room temperature overnight
  4. customThe reaction was quenched with saturated NH4Cl (10 mL) and conc. ammonia (10 mL)
  5. additionDiethyl ether (80 mL) was added
  6. filtrationthe mixture was filtered through Celite
  7. extractionThe aqueous phase was extracted twice with diethyl ether
  8. washThe combined organic phases were washed once with brine
  9. dry with materialdried (MgSO4)
  10. customThe solvent was evaporated
  11. customthe crude product was chromatographed on silica (petroleum ether-ethyl acetate 3:1)
  12. customaffording a yellow oil, 3.75 g (73%)

出典と根拠

ORDレコード
ord-7d8c3fcafa8c48e68ccc416205efb9e8
出典データセット
uspto-grants-2001_11
特許番号
US06313132B1

関連ノート

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