2-(4-Hydroxyphenyl)-5-benzofurancarboxylic acid → HCID 10192749, compound

HRID 1794555Notes

Reaction equation

HRID 1794555 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][C:14]([C:17](O)=[O:18])=[CH:13][C:11]=3[CH:12]=2)=[CH:4][CH:3]=1>C1COCC1>[OH:18][CH2:17][C:14]1[CH:15]=[CH:16][C:10]2[O:9][C:8]([C:5]3[CH:6]=[CH:7][C:2]([OH:1])=[CH:3][CH:4]=3)=[CH:12][C:11]=2[CH:13]=1

Participants

3

Reactant 1

HCID 222216192-(4-Hydroxyphenyl)-5-benzofurancarboxylic acid

Product 1

HCID 10192749HCID 10192749, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Compound 143 (0.21 g, 0.83 mmol) in THF (10 ml) was treated with BH3 THF (4.0 ml of 1.0 M) and the reaction was heated to reflux. After 2 hr, the reaction was cooled and then poured into 2NHCl and extracted with EtOAc. The organic layer was dried, concentrated and the product was purified by cloumn chromatography (60% EtOAc/Hexane) to give 144 as a solid (0.07 g, 37%); Mp=248–250° C.; 1H NMR (DMSO-d6) δ 9.86 (br s, 1 H), 7.72 (d, 2 H, J=8.3 Hz), 7.52–7.49 (m, 2 H), 7.19 (dd, 1 H, J=8.3 Hz, 1.6 Hz), 7.15 (s, 1 H), 6.87 (d, 2 H, J=8.8 Hz), 5.19 (t, 1 H, J=5.2 Hz), 4.56 (d, 2 H, J=4.1 Hz); MS 239 (M−H)−.

Workup

  1. temperaturethe reaction was heated to reflux
  2. temperaturethe reaction was cooled
  3. additionpoured into 2NHCl and
  4. extractionextracted with EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated
  7. customthe product was purified by cloumn chromatography (60% EtOAc/Hexane)

Sources & evidence

ORD record
ord-fdf7a05dbb194648b2c70f192899c877
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

Loading…