Piperidine → 4-hydroxy-5-(2-isopropyl-5-methyl-phenyl)sulfanyl-2,2-diphenyl-3H-pyran-6-one

HRID 357866Notes

Reaction equation

HRID 357866 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]=[CH:25][C:26]([CH:30]([CH3:32])[CH3:31])=[C:27]([SH:29])[CH:28]=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:29][C:27]1[CH:28]=[C:23]([CH3:22])[CH:24]=[CH:25][C:26]=1[CH:30]([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 212225182-Isopropyl-5-methylbenzenethiolHCID 547215603-bromo-5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Product 1

HCID 546890174-hydroxy-5-(2-isopropyl-5-methyl-phenyl)sulfanyl-2,2-diphenyl-3H-pyran-6-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in General Method 6 from 2.0 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one (prepared in example AAA), 2.1 mmol of 5-methyl-2-isopropylbenzenethiol, and 2.1 mmol of piperidine in 30 mL of dichloromethane. The product was chromatographed on silica gel, eluting first with chloroform and then with 5% methanol in chloroform (m.p. 183°-184° C.). 1H NMR (DMSO-d6) δ 1.15 (d, 6 H), 1.85 (s, 3 H), 3.22 (m, 1 H), 3.80 (bs, 2 H), 5.88 (bs, 1 H), 6.77 (d, 1 H), 7.03 (d, 1 H), 7.32-7.47 (m, 10 H).

Workup

  1. customThe product was chromatographed on silica gel
  2. washeluting first with chloroform

Sources & evidence

ORD record
ord-2216399a09d241e886a791b668b1f889
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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