Piperidine → 4-hydroxy-2,2-diphenyl-5-(2-sec-butylphenyl)sulfanyl-3H-pyran-6-one

HRID 357861Notes

Reaction equation

HRID 357861 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].[CH:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[SH:32])([CH2:24][CH3:25])[CH3:23].N1CCCCC1>ClCCl>[CH:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[S:32][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])([CH2:24][CH3:25])[CH3:23]

Participants

5

Reactant 3

HCID 8082PiperidineHCID 2407042-Sec-butylbenzenethiolHCID 547215603-bromo-5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one

Product 1

HCID 546890144-hydroxy-2,2-diphenyl-5-(2-sec-butylphenyl)sulfanyl-3H-pyran-6-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared as described in General Method 6 from 1.6 mmol of 3-bromo-5,6-dihydro-4-hydroxy-6,6-diphenyl-2H-pyran-2-one (prepared in example AAA), 1.7 mmol of 2-sec-butylbenzenethiol, and 1.7 mmol of piperidine in 25 mL of dichloromethane. The product was chromatographed on silica gel, eluting first with chloroform and then with 5% methanol in chloroform, to give the title compound (m.p. 161°-162° C.). 1H NMR (DMSO-d6) δ 0.81 (t, 3 H), 1.15 (d, 3 H), 1.43-1.64 (m, 2 H), 2.98 (m, 1 H), 3.77 (s, 2 H), 5.65 (dd, 1 H), 6.47 (t, 1 H), 6.92 (t, 1 H), 7.07 (d, 1 H), 7.34-7.48 (m, 10 H), 12.4 (bs, 1 H).

Workup

  1. customThe title compound was prepared
  2. customThe product was chromatographed on silica gel
  3. washeluting first with chloroform

Sources & evidence

ORD record
ord-fdeddb3118ab4f15b0135b22f7828b65
Source dataset
uspto-grants-1998_11
Patent number
US05840751

Reaction notes

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