Chlorotrimethylsilane → HCID 11255491、化合物

HRID 2058295ノート

反応式

HRID 2058295 の反応式
C(NC(C)C)(C)C.C([Li])CCC.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][CH:15]=1.[CH3:24][Si:25]([CH3:28])([CH3:27])Cl>O1CCCC1.CCCCCC>[CH3:24][Si:25]([CH3:28])([CH3:27])[O:22][C:21]([O:23][Si:25]([CH3:28])([CH3:27])[CH3:24])=[CH:20][C:17]1[CH:16]=[CH:15][C:14]([Cl:13])=[CH:19][CH:18]=1

参加物

7

反応物 4

HCID 6397ChlorotrimethylsilaneHCID 7912DiisopropylamineHCID 15880(4-Chlorophenyl)acetic acidHCID 178418339Butyllithium

生成物 1

HCID 11255491HCID 11255491、化合物収率 52%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

A cooled (0°-5° C.) solution of 41.4 g (0.41 mol) of diisopropylamine in 300 ml of tetrahydrofuran was treated slowly with butyllithium in hexane (250 ml of a 1.6 M solution, 0.4 mol). A solution of 34.12 g (0.2 mol) of p-chlorophenylacetic acid in 200 ml of tetrahydrofuran was added dropwise and the reaction mixture was stirred 30 minutes at 0° C. Trimethylchlorosilane (100 g) was added and the mixture was allowed to warm to room temperature and was stirred for 1.5 hours. The contents of the flask were filtered under nitrogen and the filtrate was evaporated under reduced pressure. The residue was dissolved in 80 ml of diethyl ether; the solution was filtered and the filtrate was evaporated. The resultant residue was distilled in a Vigreux column, maintaining the pot temperature below 130° C. to prevent decomposition of the product. The product β,β-bis(trimethylsiloxy)p-chlorostyrene, 32.56 g (52% yield), was obtained as a colorless liquid, bp 110° C. (0.1 mm); 1H NMR (CDCl3) δ7.0-7.4 (m, 4H), δ4.52 (s, 1H); δ0.22 (s) and δ0.26 (s) together 18H. The moisture sensitive product was stored under nitrogen.

後処理

  1. temperatureto warm to room temperature
  2. stirringwas stirred for 1.5 hours
  3. filtrationThe contents of the flask were filtered under nitrogen
  4. customthe filtrate was evaporated under reduced pressure
  5. dissolutionThe residue was dissolved in 80 ml of diethyl ether
  6. filtrationthe solution was filtered
  7. customthe filtrate was evaporated
  8. distillationThe resultant residue was distilled in a Vigreux column
  9. temperaturemaintaining the pot temperature below 130° C.

出典と根拠

ORDレコード
ord-25c221e8f329414f900d69f181dc0101
出典データセット
uspto-grants-1980_07
特許番号
US04215044

反応ノート

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