Isobutylene → HCID 22261682, compound

HRID 413427Notes

Reaction equation

HRID 413427 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[CH:6]=1)[CH3:2].[CH3:13][C:14](=[CH2:16])[CH3:15].OS(C(F)(F)F)(=O)=O.CCN(CC)CC>C(Cl)Cl>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:14]([CH3:16])([CH3:15])[CH3:13])[CH:6]=1)[CH3:2]

Participants

6

Reactant 4

HCID 8255IsobutyleneHCID 8471TriethylamineHCID 24522Ethyl 3-hydroxybenzoateHCID 62406Trifluoromethanesulfonic acid

Product 1

HCID 22261682HCID 22261682, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

Into a solution of 3-hydroxy-benzoic acid ethyl ester (10.14 g, 0.061 mol) in CH2Cl2 (200 mL) cooled to −78° C. was condensed isobutylene (150 mL) followed by addition of triflic acid (1.08 mL, 0.061 mol). The reaction mixture was allowed to warm to −20° C. When a solution was obtained and tlc indicated loss of starting material, the reaction was quenched with Et3N (6.8 mL, 0.049 mol) and left to warm to ambient temperature. The solution was concentrated and the residue chromatographed on an ISCO combiflash eluting with 0-10% EtoAc/hexane to give 12.91 g (95%) of the title compound.

Workup

  1. customWhen a solution was obtained
  2. waitleft
  3. temperatureto warm to ambient temperature
  4. concentrationThe solution was concentrated
  5. customthe residue chromatographed on an ISCO combiflash
  6. washeluting with 0-10% EtoAc/hexane

Sources & evidence

ORD record
ord-d398883e6780446f99684757957ae474
Source dataset
uspto-grants-2003_05
Patent number
US06566385B2

Reaction notes

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