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

HRID 1170563Notes

Reaction equation

HRID 1170563 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-a8a9e8e5fd6e46b3b62658816bcc1356
Source dataset
uspto-grants-2010_11
Patent number
US07825265B2

Reaction notes

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