Thiophenol → HCID 54688992, compound

HRID 481886Notes

Reaction equation

HRID 481886 reaction equation
Br[C:2]1[C:3](=[O:20])[O:4][C:5]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][C:7]=1[OH:8].[C:21]1([SH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.N1CCCCC1>ClCCl>[OH:8][C:7]1[CH2:6][C:5]([CH2:15][CH2:16][CH:17]([CH3:19])[CH3:18])([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[O:4][C:3](=[O:20])[C:2]=1[S:27][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7969ThiophenolHCID 8082PiperidineHCID 547217043-bromo-5,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one

Product 1

HCID 54688992HCID 54688992, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in General Method 6 from 1.5 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6-(3-methylbutyl)-6-phenyl-2H-pyran-2-one (prepared in example CCC), 1.6 mmol of benzenethiol, and 1.6 mmol of piperidine in 20 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. 154°-155° C.). 1H NMR (DMSO-d6) δ0.80 (m, 6H), 0.97 (m, 1H), 1.16 (m, 2H), 1.42 (m, 1H), 1.91 (m, 2H), 3.40 (2H+H2O), 6.45 (m, 2H), 6.93 (m, 3H), 7.37 (m, 5H).

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-a6feec52cc7844b7badd4f4aacb9b9e0
Source dataset
uspto-grants-1998_08
Patent number
US05789440

Reaction notes

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