Piperidine → 4-hydroxy-5-(2-isopropyl-5-methyl-phenyl)sulfanyl-2-phenethyl-2-phenyl-3H-pyran-6-one

HRID 357867Notes

Reaction equation

HRID 357867 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]=[CH:27][C:28]([CH:32]([CH3:34])[CH3:33])=[C:29]([SH:31])[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:29]1[CH:30]=[C:25]([CH3:24])[CH:26]=[CH:27][C:28]=1[CH:32]([CH3:34])[CH3:33]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 212225182-Isopropyl-5-methylbenzenethiolHCID 547216393-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Product 1

HCID 546890184-hydroxy-5-(2-isopropyl-5-methyl-phenyl)sulfanyl-2-phenethyl-2-phenyl-3H-pyran-6-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), 2.1 mmol of 5-methyl-2-isopropylbenzenethiol, and 2.1 mmol of piperidine in 30 mL of dichloromethane. The product was chromatographed on silica gel, eluting first with chloroform and then with 5% methanol in chloroform (m.p. 66°-67° C.). 1H NMR (DMSO-d6) δ 1.16 (m, 6 H), 1.87 (s, 3 H), 2.26 (m, 3 H), 2.57 (m, 1 H), 3.23 (m, 1 H), 3.43 (q, 2 H), 6.01 (bs, 1 H), 6.78 (d, 1 H), 7.03-7.27 (m, 6 H), 7.37-7.47 (m, 5 H).

Workup

  1. customThe product was chromatographed on silica gel
  2. washeluting first with chloroform

Sources & evidence

ORD record
ord-583bff4d2fd54e288f236636a5317eeb
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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