Benzyl mercaptan → HCID 54681185, compound

HRID 613150Notes

Reaction equation

HRID 613150 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.[CH:19](=O)[CH2:20][CH:21]([CH3:23])[CH3:22].[CH2:25]([SH:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.N1CCCCC1>C(O)(=O)C.C(O)C>[CH2:25]([S:32][CH:19]([C:3]1[C:4](=[O:18])[O:5][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)=[CH:7][C:2]=1[OH:1])[CH2:20][CH:21]([CH3:23])[CH3:22])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

7

Reactant 4

HCID 7509Benzyl mercaptanHCID 8082PiperidineHCID 115523-MethylbutanalHCID 54681503HCID 54681503, compound

Product 1

HCID 54681185HCID 54681185, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

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), isovaleraldehyde (0.35 g, 4.06 mmol), benzylmercaptan (1.0 g, 8.12 mmol), piperidine (0.5 mL), acetic acid (0.5 mL). 1H NMR (400 MHz, DMSO-d6) δ0.78 (t, 6H), 1.36 (m, 1H), 1.5 (m, 1H), 2.06 (m, 1H), 4.2 (m, 1H), 4.31 (brm, 6H), 6.56 (s, 1H), 7.03 (d, 2H), 7.36-7.25 (m, 6H).

Sources & evidence

ORD record
ord-a3bc6cddbef5480ba44c7cb692499699
Source dataset
uspto-grants-1999_12
Patent number
US06005103

Reaction notes

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