Acetic Acid → HCID 18762001, compound

HRID 430902Notes

Reaction equation

HRID 430902 reaction equation
[OH-].[K+].[CH3:3][N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[C:9]1[CH:10]=[C:11]([C:15]#[C:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23]C)=[O:22])=[CH:19][CH:18]=2)[CH:12]=[N:13][CH:14]=1.CC(O)=O>CO>[CH3:3][N:4]1[CH2:8][CH2:7][CH2:6][CH:5]1[C:9]1[CH:10]=[C:11]([C:15]#[C:16][C:17]2[CH:18]=[CH:19][C:20]([C:21]([OH:23])=[O:22])=[CH:25][CH:26]=2)[CH:12]=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 14797Potassium HydroxideHCID 18762004HCID 18762004, compound

Product 1

HCID 18762001HCID 18762001, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

KOH (168 mg, 3 mmol) was added to YH19 (0.32 g, 1 mmol) in MeOH (5 mL). The stirred mixture was refluxed for 2 h and then cooled to room temperature. HOAc was added to pH8 and the volatiles were evaporated. The residue was chromatographed [SiO2, CHCl3/MeOH (5:1)] to give 0.19 g (62%) of YH20; 1H NMR (270 MHz, CDCl3) δ 11.00 (br s, OH), 8.75 (br s, 1H), 8.44 (m, 2H), 8.10 (d, J=8 Hz, 2H), 7.42 (d, J=8.5 Hz, 2H), 3.94-3.84 (m, 1H), 3.63-3.52 (m, 1H), 2.69-2.58 (m, 1H), 2.42 (s, 3H), 2.42-1.98 (m, 4H); 13C NMR (270 MHz, CDCl3) δ 169.5, 151.6, 148.9, 139.0, 133.8, 132.9, 131.5, 129.6, 125.3, 120.8, 93.0, 87.4, 69.0, 55.5, 38.8, 33.2, 21.7;

Workup

  1. temperatureThe stirred mixture was refluxed for 2 h
  2. customthe volatiles were evaporated
  3. customThe residue was chromatographed [SiO2, CHCl3/MeOH (5:1)]
  4. customto give 0.19 g (62%) of YH20

Sources & evidence

ORD record
ord-48e33ef6c7774680a5730edd70bf2c03
Source dataset
uspto-grants-2003_12
Patent number
US06656469B1

Reaction notes

Loading…