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

HRID 1585413Notes

Reaction equation

HRID 1585413 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].[CH3:22][C:23]1[CH:24]=[C:25]([SH:29])[CH:26]=[CH:27][CH:28]=1.N1CCCCC1>ClCCl.[OH-].[Na+]>[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:29][C:25]1[CH:26]=[CH:27][CH:28]=[C:23]([CH3:22])[CH:24]=1

Participants

6

Reactant 3

HCID 79303-ThiocresolHCID 8082PiperidineHCID 547215603-bromo-5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Product 1

HCID 547217235,6-Dihydro-4-hydroxy-3-(3-methylphenylthio)-6,6-diphenyl-2H-pyran-2-one

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

The title compound was prepared as described in General Method 6 from 1.3 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one (prepared in example AAA), 1.4 mmol of 3-methylbenzenethiol, and 1.4 mmol of piperidine in 25 mL of dichloromethane. The product was triturated with hexane:ether (1:1) to afford a solid which was dissolved in 2 N NaOH, washed with ether, acidified to pH 2, and extracted with ethyl acetate. The extract was washed with water, dried over MgSO4, and concentrated to give a solid (m.p. 58-60° C.). 1H NMR (DMSO-d6) δ 2.07 (s, 3 H), 3.77 (s, 2 H), 6.06 (m, 1 H), 6.45 (s, 1 H), 6.78 (m, 2 H), 7.25-7.47 (m, 10 H).

Workup

  1. customThe product was triturated with hexane:ether (1:1)
  2. customto afford a solid which
  3. washwashed with ether
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-b1eb3a9b5bf04b60998126c46aacfbd2
Source dataset
uspto-grants-1999_08
Patent number
US05936128

Reaction notes

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