Diethyl Ether → HCID 57203449, compound

HRID 566897Notes

Reaction equation

HRID 566897 reaction equation
CC[CH2:3][CH2:4][CH2:5][CH3:6].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[OH:15])=[CH:10][CH:9]=1.[CH3:30]COCC>CS(C)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([O:15][CH2:3][CH:4]=[C:5]([CH3:6])[CH3:30])([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)[C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 8058HexaneHCID 76379Tris(4-chlorophenyl)methanol

Product 1

HCID 57203449HCID 57203449, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Procedure

Dry DMSO (20 mL) was added to 14 mmol of hexane-washed KH under Ar with stirring at RT. After H2 evolution ceased, a solution of tris-(p-chlorophenyl) methanol (3.63 g, 10 mmol) in 25 mL dry DMSO was added, giving a deep red anion solution. After 5 min,1-bromo-3-methyl-2-butene (2.0 mL, 19 mmol) was added and stirring continued for 1 h. The crude product was isolated by Et2O extraction and purified by flash chromatography (75 g SiO2, 5% EtOAc-hexanes) giving 3.93 g (91%) of (3-methyl-2-butenyl) tris-(4-chlorophenyl)methyl ether as an oil.

Workup

  1. washwashed KH under Ar
  2. customgiving a deep red anion solution
  3. stirringstirring
  4. custompurified by flash chromatography (75 g SiO2, 5% EtOAc-hexanes)

Sources & evidence

ORD record
ord-4a75bc2f3c42416b96438feabf475e6e
Source dataset
uspto-grants-2001_01
Patent number
US06177427B1

Reaction notes

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