Methyl iodide → HCID 20401742, compound

HRID 1980516Notes

Reaction equation

HRID 1980516 reaction equation
[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

Participants

8

Reactant 5

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

Product 1

HCID 20401742HCID 20401742, compoundYield 79.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-7f16e595b5374471ab13567d7832ac11
Source dataset
uspto-grants-1985_04
Patent number
US04510136

Reaction notes

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