Tetrahydrofuran → 1-(4-Hydroxyphenyl)-2-(pyridin-4-yl)ethanone

HRID 2280256Notes

Reaction equation

HRID 2280256 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:23])[CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C1COCC1>CO>[OH:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:23])[CH2:16][C:17]2[CH:22]=[CH:21][N:20]=[CH:19][CH:18]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 109027571-(4-Benzyloxy-phenyl)-2-pyridin-4-yl-ethanone

Product 1

HCID 227070041-(4-Hydroxyphenyl)-2-(pyridin-4-yl)ethanoneYield 85.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Intermediate 1B, 1-(4-(benzyloxy)phenyl)-2-(pyridin-4-yl)ethanone (5.22 g, 17.21 mmol) and solvent THF (60 mL) were added to 20% Pd(OH)2—C, wet (1.044 g, 7.43 mmol) in a 250 mL stainless steel pressure bottle. The reaction mixture was stirred for 3 hr at 30 psi and ambient temperature. HPLC indicated that both starting material and product were present, so MeOH (10 mL) was added and the reaction was run for an additional 1 h. The reaction mixture was filtered through a nylon membrane and the filtrate was concentrated under reduced pressure to give a pale yellow solid (3.13 g, 85% yield). Much of the yellow color was removed by rinsing with MeOH. After the MeOH rinses, the solid was rinsed with Et2O, then dried in a vacuum oven at 50° C. for 4 hours. This vacuum-dried sample weighed 2.071 g (56.4%). 1H NMR (300 MHz, DMSO-d6) δ 10.38 (br s, 1H), 8.52-8.45 (m, 2H), 7.96-7.89 (m, 2H), 7.29-7.24 (m, 2H), 6.90-6.83 (m, 2H), 4.35 (s, 2H). MS (DCI—NH3) m/z=214 (M+H)+, m/z=231 (M+NH4)+.

Workup

  1. waitthe reaction was run for an additional 1 h
  2. filtrationThe reaction mixture was filtered through a nylon membrane
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ef67483eb23d4eb492dcb4e57a4b208b
Source dataset
uspto-grants-2015_09
Patent number
US09138494B2

Reaction notes

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