Ethanol → HCID 54681216, compound

HRID 613148Notes

Reaction equation

HRID 613148 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:17]=[CH:16][C:11]3[O:12][CH2:13][CH2:14][O:15][C:10]=3[CH:9]=2)[O:5][C:4](=[O:18])[CH:3]=1.C(O)C.[CH2:22]1[CH2:26][CH:25]([SH:27])[CH2:24][CH2:23]1.N1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C(O)(=O)C>[CH:25]1([S:27][CH:29]([C:3]2[C:4](=[O:18])[O:5][C:6]([C:8]3[CH:17]=[CH:16][C:11]4[O:12][CH2:13][CH2:14][O:15][C:10]=4[CH:9]=3)=[CH:7][C:2]=2[OH:1])[CH2:30][CH:31]2[CH2:33][CH2:32]2)[CH2:26][CH2:22][CH2:23][CH2:24]1

Participants

6

Reactant 4

HCID 702EthanolHCID 8082PiperidineHCID 15510CyclopentanethiolHCID 54681503HCID 54681503, compound

Product 1

HCID 54681216HCID 54681216, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The title compound was prepared by Method C using 4-hydroxy-6-(2,3-dihydrobenzo[1,4]dioxin-6-yl)-2H-pyran-2-one (1.00 g, 4.06 mmol), ethanol (15 mL), cyclopropylmethylcarboxaldehyde (0.34 g, 4.06 mmol), cyclopentylthiol (0.83 g, 8.12 mmol), piperidine (1.0 mL), acetic acid (1.0 mL). m.p. 80-82° C.; 1H NMR (400 MHz, DMSO-d6) δ0.03 (m, 2H), 0.33 (m, 2H), 0.64 (m, 1H), 1.28-1.74 (m, 7H), 1.83-2.06 (m, 3H), 3.06 (m, 1H), 4.2 (m, 1H), 4.31 (m, 4H), 6.53 (s, 1H), 7.0 (d, 1H), 7.24 (d, 1H), 7.24 (dd, 2H).

Sources & evidence

ORD record
ord-84592bdb4e67490ea4cf7b6616e81f17
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

Loading…