Iodine → HCID 59595858, compound

HRID 2075158Notes

Reaction equation

HRID 2075158 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][CH:8]=[CH:7][C:6]=2[CH:10]=1.II.[O:13]1[CH:18]=[CH:17][C:16](=[O:19])[CH:15]=[CH:14]1>C1COCC1>[O:9]1[C:5]2[CH:4]=[CH:3][C:2]([C:16]3([OH:19])[CH2:17][CH2:18][O:13][CH2:14][CH2:15]3)=[CH:10][C:6]=2[CH:7]=[CH:8]1

Participants

5

Reactant 3

HCID 807IodineHCID 79684H-pyran-4-oneHCID 90015Benzofuran, 5-bromo-

Product 1

HCID 59595858HCID 59595858, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-40 °C

Procedure

To a suspension of Mg (550 mg, 23.0 mmol) in dry THF (15 mL), under nitrogen atmosphere was added 5-bromobenzofuran (3.9 g, 20.0 mmol) in one portion. A crystal of iodine was added and then the contents were refluxed for 3 h. The reaction was then allowed to attain ambient temperature, and then cooled to −40° C. Pyran-4-one (3.0 g, 30.0 mmol) was added drop-wise and the resulting solution was allowed to reach room temperature. The reaction mixture was quenched by addition of 1N HCl (5 mL) and then was diluted with ether (30 mL). It was washed with water (2×15 mL) and the combined organic extract was washed with brine (15 mL), dried and concentrated under reduced pressure to give the crude carbinol as colorless oil. Purification by column chromatography using 5% EtOAc-hexanes afforded the desired product as white solid (41%). 1H NMR (400 MHz, CDCl3) δ 7.74 (d, 1H), 7.64 (d, 1H), 7.51-7.44 (m, 2H), 6.78 (d, 1H), 4.00-3.88 (m, 4H), 2.25 (t, 2H), 1.78-1.74 (m, 2H).

Workup

  1. temperaturethe contents were refluxed for 3 h
  2. customto attain ambient temperature
  3. customto reach room temperature
  4. customThe reaction mixture was quenched by addition of 1N HCl (5 mL)
  5. additionwas diluted with ether (30 mL)
  6. washIt was washed with water (2×15 mL)
  7. extractionthe combined organic extract
  8. washwas washed with brine (15 mL)
  9. customdried
  10. concentrationconcentrated under reduced pressure
  11. customto give the crude carbinol as colorless oil
  12. customPurification by column chromatography

Sources & evidence

ORD record
ord-6c5011742be64eb99798ae8537dd8bfb
Source dataset
uspto-grants-2011_04
Patent number
US07919519B2

Reaction notes

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