Methyl iodide → HCID 20401742、化合物

HRID 2413305ノート

反応式

HRID 2413305 の反応式
[C:1]1([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH2:10][Cl:11])([CH3:9])[CH3:8])=[CH:3][CH:2]=1.[CH:18]([Li])(CC)C.CN(C)CCN(C)C.CI.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[C:1]1([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:6]=[CH:5][C:4]([Si:7]([CH3:8])([CH3:9])[CH:10]([Cl:11])[CH3:18])=[CH:3][CH:2]=1

参加物

8

反応物 5

HCID 6328Methyl iodideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 25517Ammonium ChlorideHCID 13392351HCID 13392351、化合物HCID 178418400CID 53628100

生成物 1

HCID 20401742HCID 20401742、化合物収率 79.2%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒

実験手順

A solution of 4.0 g (15.3 mmol) of (1,1'-biphenyl-4-yl)chloromethyldimethylsilane in 20 ml of tetrahydrofuran was cooled to -78°, and 12.5 ml (16.8 mmol) of 1.35 molar sec-butyllithium in hexane was slowly dripped in followed by addition of 2.42 ml (16.1 mmol) of tetramethylethylenediamine. After stirring for one hour at -78°, the solution was warmed to -55° and 1.43 ml (22.9 mmol) of methyl iodide in 5 ml of tetrahydrofuran was added dropwise. The mixture was stirred another 30 minutes at -50°, warmed to room temperature, poured into saturated aqueous ammonium chloride, and extracted with ether. The ether extracts were washed with water and brine, dried over magnesium sulfate, and evaporated to give 3.33 g (65%) of the title compound contaminated by about 18% of an impurity: nmr (CDCl3) 0.3 (s, 2.7H, impurity), 0.4 (6H, s), 1.5 (3H, d, J=7 Hz), 3.5 (1H, q, J=7 Hz) and 7.3-7.7 (m, 13H).

後処理

  1. temperaturethe solution was warmed to -55°
  2. stirringThe mixture was stirred another 30 minutes at -50°
  3. extractionextracted with ether
  4. washThe ether extracts were washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated

出典と根拠

ORDレコード
ord-45e2a6e024de47bb8760fd5d50305e06
出典データセット
uspto-grants-1985_01
特許番号
US04496551

反応ノート

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