Hydrochloric Acid → HCID 10285953, compound

HRID 1794543Notes

Reaction equation

HRID 1794543 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 1.0 M 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-87a2cb507e9c403fb53ac14915ecc1f3
Source dataset
uspto-grants-2006_04
Patent number
US07022733B2

Reaction notes

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