Sulfuryl chloride → 5-chloro-2-[2-(5-chloro-2,4-dimethoxy-phenyl)ethyl]-2-cyclopentyl-4-hydroxy-3H-pyran-6-one

HRID 859716Notes

Reaction equation

HRID 859716 reaction equation
[Cl:1][C:2]1[C:3]([O:25][CH3:26])=[CH:4][C:5]([O:23][CH3:24])=[C:6]([CH2:8][CH2:9][C:10]2([CH:18]3[CH2:22][CH2:21][CH2:20][CH2:19]3)[O:15][C:14](=[O:16])[CH2:13][C:12](=[O:17])[CH2:11]2)[CH:7]=1.S(Cl)([Cl:30])(=O)=O>ClCCl>[Cl:30][C:13]1[C:14](=[O:16])[O:15][C:10]([CH2:9][CH2:8][C:6]2[CH:7]=[C:2]([Cl:1])[C:3]([O:25][CH3:26])=[CH:4][C:5]=2[O:23][CH3:24])([CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[CH2:11][C:12]=1[OH:17]

Participants

4

Reactant 2

HCID 24648Sulfuryl chlorideHCID 167287016-[2-(5-Chloro-2,4-dimethoxy-phenyl)ethyl]-6-cyclopentyl-tetrahydropyran-2,4-dione

Product 1

HCID 546895495-chloro-2-[2-(5-chloro-2,4-dimethoxy-phenyl)ethyl]-2-cyclopentyl-4-hydroxy-3H-pyran-6-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The title compound was prepared by chlorination of 6-[2-(5-chloro-2,4-dimethoxy-phenyl)-ethyl]-6-cyclopentyl-dihydro-pyran-2,4-dione from step 6 of example B(15) with sulfuryl chloride in dichloromethane at room temperature. 1H NMR (CDCl3) δ 1.51 (m, 8H), 1.79 (m, 1H), 2.06, (m, 2H), 2.45 (m, 2H), 2.60 (m, 1H), 2.67 (d, J=17.75, 1H), 2.92 (d, J=17.75, 1H), 3.82 (s, 3H), 3.92 (s, 3H), 6.44 (s, 1H), 7.06 (s, 1H). HRMS calcd for C20H24O5Cl2 (M+H+) 415.1079, found 415.1063.

Workup

  1. customat room temperature

Sources & evidence

ORD record
ord-fe7816bb44a54447912e3dfd3614a955
Source dataset
uspto-grants-2006_12
Patent number
US07151105B2

Reaction notes

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