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

HRID 357852Notes

Reaction equation

HRID 357852 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 2N 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-5650b76861f344d693db8143f35b2a7e
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

Loading…