Tetrahydrofuran → HCID 23582459, compound

HRID 1479781Notes

Reaction equation

HRID 1479781 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2O)[C:9](=O)[C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C1C[O:28]CC1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[C:18]2[CH:23]=[CH:22][C:21]([OH:28])=[CH:20][CH:19]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 8028TetrahydrofuranHCID 66822583HCID 66822583, compound

Product 1

HCID 23582459HCID 23582459, compoundYield 92%

Procedure

Compound N-(4-fluorophenyl)-4-hydroxy-N-(hydroxyphenyl)benzamide (0.30 g, 0.93 mmol) was dissolved in 20 mL anhydrous THF at room temperature. H3B(SMe2) (1.86 mL of 2M THF solution, 3.71 mmol) was added via a syringe at room temperature under argon. The reaction solution was stirred and heated to reflux for 6 hours. Then, the reaction was quenched by adding 10 mL of MeOH at 0° C. The solvent was removed under reduced pressure. The residue was subjected to flash column chromatography (silica-gel, CH2Cl2/MeOH=9/1 v/v) to give a yellow oil, 0.26 g, 92% yield. 1H NMR (DMSO-d6, 500 MHz) δ 9.29 (s, 1H), 9.24 (s, 1H), 7.09 (d, 2H, J=8.3 Hz), 6.98 (d, 2H, J=9.0 Hz), 6.94-6.91 (m, 2H), 6.73 (d, 2H, J=9.0 Hz), 6.68-6.64 (m, 4H), 4.70 (s, 2H). MS m/z 307.8 (M−H)−.

Workup

  1. temperatureheated
  2. temperatureto reflux for 6 hours
  3. customThen, the reaction was quenched
  4. additionby adding 10 mL of MeOH at 0° C
  5. customThe solvent was removed under reduced pressure
  6. customto give a yellow oil, 0.26 g, 92% yield

Sources & evidence

ORD record
ord-5cfd12522a814ff1bc8b91688dfd342c
Source dataset
uspto-grants-2016_08
Patent number
US09409856B2

Reaction notes

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