3-Thiocresol → 5,6-Dihydro-4-hydroxy-3-(3-methylphenylthio)-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

HRID 357855Notes

Reaction equation

HRID 357855 reaction equation
Br[C:2]1[C:3](=[O:23])[O:4][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:6][C:7]=1[OH:8].[CH3:24][C:25]1[CH:26]=[C:27]([SH:31])[CH:28]=[CH:29][CH:30]=1.N1CCCCC1>ClCCl>[OH:8][C:7]1[CH2:6][C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)([CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:4][C:3](=[O:23])[C:2]=1[S:31][C:27]1[CH:28]=[CH:29][CH:30]=[C:25]([CH3:24])[CH:26]=1

Participants

5

Reactant 3

HCID 79303-ThiocresolHCID 8082PiperidineHCID 547216393-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Product 1

HCID 547215485,6-Dihydro-4-hydroxy-3-(3-methylphenylthio)-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in General Method 6 from 2.0 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (prepared in example BBB), 2.2 mmol of 3-methylbenzenethiol, and 2.2 mmol of piperidine in 30 mL of dichloromethane. The crude product was chromatographed on silica gel, eluting first with chloroform and then with 5% methanol in chloroform, to give the title compound (m.p. 68°-70° C.). 1H NMR (DMSO-d6) δ 2.06 (s, 3 H), 2.18-2.36 (m, 3 H), 2.60 (m, 1 H), 3.38 (2 H+H2O), 6.26 (d, 1 H), 6.46 (s, 1 H), 6.75 (m, 1 H), 6.83 (t, 1 H), 7.15 (m, 3 H), 7.24 (m, 2 H), 7.45 (m, 5 H).

Workup

  1. customThe title compound was prepared
  2. customThe crude product was chromatographed on silica gel
  3. washeluting first with chloroform

Sources & evidence

ORD record
ord-6094926be78d4dd390aa8da597b50e7f
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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