Hydrochloric Acid → HCID 10192749, compound

HRID 1836060Notes

Reaction equation

HRID 1836060 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.Cl>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

4

Reactant 2

HCID 313Hydrochloric AcidHCID 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 1.0M) and the reaction was heated to reflux. After 2 hr, the reaction was cooled and then poured into 2N HCl 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°; 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. extractionextracted with EtOAc
  4. customThe organic layer was dried
  5. concentrationconcentrated
  6. customthe product was purified by cloumn chromatography (60% EtOAc/Hexane)

Sources & evidence

ORD record
ord-bf9ac396461c45feb5091c6a65ac59f7
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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