Thiophenol → 4-hydroxy-2-phenethyl-2-phenyl-5-phenylsulfanyl-3H-pyran-6-one

HRID 357853Notes

Reaction equation

HRID 357853 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].[C:24]1([SH:30])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=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:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8082PiperidineHCID 547216393-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one

Product 1

HCID 546890014-hydroxy-2-phenethyl-2-phenyl-5-phenylsulfanyl-3H-pyran-6-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in General Method 6 from 1.50 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6-phenyl-6-(2-phenylethyl)-2H-pyran-2-one (prepared in example BBB), 1.60 mmol of benzenethiol, and 1.60 mmol of piperidine in 30 mL of dichloromethane. The product was triturated with hexane:ether (1:1) to afford a solid. 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. 58°-60° C.). 1H NMR (DMSO-d6) δ 2.22-2.39 (m, 3 H), 2.62 (m, 1 H), 3.46 (q, 2 H), 6.48 (m, 2 H), 6.98 (m, 3 H), 7.15 (m, 3 H), 7.25 (m, 2 H), 7.46 (m, 5 H).

Workup

  1. customThe title compound was prepared
  2. customThe product was triturated with hexane:ether (1:1)
  3. customto afford a solid
  4. customThe crude product was chromatographed on silica gel
  5. washeluting first with chloroform

Sources & evidence

ORD record
ord-f2de503544f04a718867fa4ea7235a07
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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