Iodine → HCID 59595858, compound

HRID 2264560Notes

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

Conditions

Temperature: -40 °C

Procedure

To a suspension of Mg (550 mg, 23.0 mmol) in dry THF (I5mL), 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 3h. 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

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

Sources & evidence

ORD record: ord-095170b0bf214693bc8a0e878d4a09e6
Source dataset: uspto-grants-2010_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07855193B2

Reaction notes

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