Ethanol → HCID 69945585, compound

HRID 613147Notes

Reaction equation

HRID 613147 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=2)[O:5][C:4](=[O:19])[CH:3]=1.[CH2:20](O)C.[CH2:23]1[CH2:27][CH:26]([SH:28])[CH2:25][CH2:24]1.N1[CH2:34][CH2:33][CH2:32][CH2:31]C1>C(O)(=O)C>[CH2:17]([O:16][C:14](=[O:15])[C:11]1[CH:10]=[CH:9][C:8]([C:6]2[O:5][C:4](=[O:19])[C:3]([CH:31]([S:28][CH:26]3[CH2:27][CH2:23][CH2:24][CH2:25]3)[CH2:32][CH:33]([CH3:34])[CH3:20])=[C:2]([OH:1])[CH:7]=2)=[CH:13][CH:12]=1)[CH3:18]

Participants

6

Reactant 4

HCID 702EthanolHCID 8082PiperidineHCID 15510CyclopentanethiolHCID 54730478HCID 54730478, compound

Product 1

HCID 69945585HCID 69945585, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared by Method C using 4-hydroxy-6-(4'-carbethoxyphenyl)-2H-pyran-2-one (1.50 g, 5.77 mmol), ethanol (15 mL), isovalaraldehyde (0.497 g, 5.77 mmol), cyclopentylthiol (1.18 g, 11.54 mmol), piperidine (1.0 mL), acetic acid (1.0 mL). m.p. 174-176° C; 1H NMR (400 MHz, DMSO-d6) δ1.05-0.72 (m, 10H), 1.81-1.14(m, 7H), 2.13-1.81(m, 3H), 3.04 (t, 1H), 4.22 (m, 1H), 4.36 (q, 2H), 6.8 (s, 1H), 7.90 (d, 1H), 7.97 (q, 1H), 8.15 (m, 2H).

Sources & evidence

ORD record
ord-0eb16d34f01e4363b224468d2b7b7d13
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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