Hydrochloric Acid → HCID 10285953, compound

HRID 1836047Notes

Reaction equation

HRID 1836047 reaction equation
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]([C:10]3[CH:18]=[CH:17][C:13]([C:14](O)=[O:15])=[CH:12][CH:11]=3)=[CH:7][C:6]=2[CH:19]=1.Cl>C1COCC1>[OH:15][CH2:14][C:13]1[CH:12]=[CH:11][C:10]([C:8]2[O:9][C:5]3[CH:4]=[CH:3][C:2]([OH:1])=[CH:19][C:6]=3[CH:7]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 101492294-(5-Hydroxy-benzofuran-2-yl)-benzoic acid

Product 1

HCID 10285953HCID 10285953, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 128 (0.15 g, 0.6 mmol), in THF (20 ml) was added BH3 (3 ml of 1.0M in THF) and the reaction was heated to reflux for 3 hr. The reaction was then cooled and poured into 2N HCl and extracted with EtOAc. The EtOAc was dried over MgSO4, filtered and concentrated and triturated with CH2Cl2 and filtered to give 129 as a solid (0.08 g, 57%); 1H NMR (DMSO-d6) δ 9.21 (br s, 1 H), 7.82 (d, 2 H, J=8.1 Hz), 7.43-7.38 (m, 3 H), 7.24 (s, 1 H), 6.92 (d, 1 H, J=2.1 Hz), 6.73 (dd, 1 H, J=8.5 Hz, 2.6 Hz), 5.28 (t, 1 H, J=5.7 Hz), 4.54 (d, 2 H, J=5.5 Hz); MS 239 (M−H)−.

Workup

  1. temperaturethe reaction was heated
  2. temperatureto reflux for 3 hr
  3. temperatureThe reaction was then cooled
  4. extractionextracted with EtOAc
  5. dry with materialThe EtOAc was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customtriturated with CH2Cl2
  9. filtrationfiltered

Sources & evidence

ORD record
ord-2815a4012831496cae4ce467fcf76b64
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

Loading…