Thiophenol → 4-hydroxy-2,2-diphenyl-5-phenylsulfanyl-3H-pyran-6-one

HRID 357851Notes

Reaction equation

HRID 357851 reaction equation
Br[C:2]1[C:3](=[O:21])[O:4][C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][C:7]=1[OH:8].[C:22]1([SH:28])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.N1CCCCC1>ClCCl>[OH:8][C:7]1[CH2:6][C:5]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:4][C:3](=[O:21])[C:2]=1[S:28][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8082PiperidineHCID 547215603-bromo-5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Product 1

HCID 546889864-hydroxy-2,2-diphenyl-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 0.96 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one (prepared in example AAA), 1.0 mmol of benzenethiol, and 1.0 mmol of piperidine in 20 mL of dichloromethane. The product was triturated with hexane:ether (1:1) to afford a solid (m.p. 78°-80° C.). 1H NMR (DMSO-d6) δ 3.37 (bs, 2 H), 6.35 (m, 2 H), 6.93 (m, 3 H), 7.29-7.49 (m, 10 H).

Workup

  1. customThe product was triturated with hexane:ether (1:1)

Sources & evidence

ORD record
ord-fbeddebb631e448fb668adc3fa2f87b4
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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