Methyl iodide → HCID 20401742, 화합물

HRID 1980516노트

반응식

HRID 1980516 반응식
[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

참가 물질

8

반응물 5

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

생성물 1

HCID 20401742HCID 20401742, 화합물수율 79.2%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7f16e595b5374471ab13567d7832ac11
출처 데이터셋
uspto-grants-1985_04
특허 번호
US04510136

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