Water → Ctk1B5122

HRID 41157

Reaction equation

HRID 41157 reaction equation
F[B-](F)(F)F.[H+].C(O)(=O)C.C(O)(=O)C.IC1C=CC=CC=1.[CH:22]1([CH2:27][C:28]([OH:30])=[O:29])[CH2:26][CH2:25][CH:24]=[CH:23]1.O>C(O)(=O)C>[O:29]1[C:28](=[O:30])[CH2:27][C@@H:22]2[CH2:26][CH:25]=[CH:24][C@H:23]12

Participants

6

Reactant 4

HCID 962WaterHCID 28118Tetrafluoroboric acidHCID 962162-Cyclopentene-1-acetic acidHCID 12217721Iodo benzene diacetate

Product 1

HCID 11126247Ctk1B5122

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Tetrafluoroboric acid (2.50 mL, 15.9 mmol) was added to a solution of iodobenzene diacetate (5.10 g, 15.9 mmol) in acetic acid (13.2 mL). 2-Cyclopentene-1-acetic acid (955 μL, 7.93 mmol) was added and the solution was stirred at room temperature for 1 hour. The solution was then added to water and extracted with chloroform. The chloroform layer was extracted with water. The combined organic layers were dried (magnesium sulfate), filtered, and concentrated in vacuo. The residue was purified by silica gel chromatography (Biotage 40M), eluting with 0-100% ethyl acetate/hexanes to give the title compound as a colorless oil. 1H NMR (500 MHz, CHCl3) δ 2.22-2.31 (m, 2H), 2.67-2.84 (m, 2H), 3.05-3.15 (m, 1H), 5.44-5.51 (m, 1H), 5.79-5.86 (m, 1H), 6.01-6.07 (m, 1H).

Workup

  1. extractionextracted with chloroform
  2. extractionThe chloroform layer was extracted with water
  3. dry with materialThe combined organic layers were dried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography (Biotage 40M)
  7. washeluting with 0-100% ethyl acetate/hexanes

Sources & evidence

ORD record
ord-7aaa0f4440d44075bea17a6b45e2a5f2
Source dataset
uspto-grants-2013_09
Patent number
US08530521B2

Linked notes

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