Diethyl Ether → HCID 57203449, compound

HRID 1004568Notes

Reaction equation

HRID 1004568 reaction equation
CCCCCC.[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.Br[CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34].CCOCC>CS(C)=O>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]([O:15][CH2:31][CH:32]=[C:33]([CH3:35])[CH3:34])([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

6

Reactant 4

HCID 3283Diethyl EtherHCID 8058HexaneHCID 700922-Butene, 1-bromo-3-methyl-HCID 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. waitcontinued for 1 h
  5. custompurified by flash chromatography (75 g SiO2, 5% EtOAc-hexanes)

Sources & evidence

ORD record
ord-2e90edacc24445b5a1937ef7fd608116
Source dataset
uspto-grants-2000_04
Patent number
US06051573

Reaction notes

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