1-Cyclohexenyl trifluoromethanesulfonate → 3-(Cyclohex-1-en-1-yl)thiophene

HRID 70741Notes

Reaction equation

HRID 70741 reaction equation
[S:1]1[CH:5]=[CH:4][C:3](B(O)O)=[CH:2]1.O([C:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=1)S(C(F)(F)F)(=O)=O>CCOCC.C([O-])([O-])=O.[Na+].[Na+].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[S:1]1[CH:5]=[CH:4][C:3]([C:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH:18]=2)=[CH:2]1

Participants

6

Reactant 2

HCID 3194401-Cyclohexenyl trifluoromethanesulfonateHCID 581760Thiophene-3-boronic acid

Product 1

HCID 126474723-(Cyclohex-1-en-1-yl)thiopheneYield 91.3%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 3283Diethyl EtherSolventHCID 10340Sodium CarbonateSolvent

Procedure

3-Thiophene boronic acid (128 mg, 1.00 mmol), cyclohexenyl triflate (230.2 mg, 1.00 mmol) was dissolved in Et2O (4 mL) and 2M Na2CO3 (1 mL). The mixture was degassed and Pd(PPh3)4 (0.05 mmol) added. After stirring at room temperature for 4 h the mixture was filtered through celite, rinsed with Et2O, dried (Na2SO4) and subjected to column chromatography (silica, pentane) to yield 150 mg of a volatile liquid. GC-MS: M+=164.

Workup

  1. customThe mixture was degassed
  2. filtrationwas filtered through celite
  3. washrinsed with Et2O
  4. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-a705f71dfea34badb6cc493f161878ee
Source dataset
uspto-grants-2014_09
Patent number
US08822548B2

Reaction notes

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