Pyridine → 8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate

HRID 20627

Reaction equation

HRID 20627 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[CH:12]1([O:17][C:18]2[C:19]([O:30][CH3:31])=[CH:20][CH:21]=[C:22]3[C:27]=2[O:26][C:25](=[O:28])[CH:24]=[C:23]3[OH:29])[CH2:16][CH2:15][CH2:14][CH2:13]1.N1C=CC=CC=1>ClCCl>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([O:29][C:23]2[C:22]3[C:27](=[C:18]([O:17][CH:12]4[CH2:13][CH2:14][CH2:15][CH2:16]4)[C:19]([O:30][CH3:31])=[CH:20][CH:21]=3)[O:26][C:25](=[O:28])[CH:24]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 771747928-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one

Product 1

HCID 866181328-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4-Methylbenzene-1-sulfonyl chloride (135 mg, 0.71 mmol) was added to a solution of 8-(cyclopentyloxy)-4-hydroxy-7-methoxy-2H-chromen-2-one (175 mg, 0.63 mmol), pyridine (0.15 mL, 1.85 mmol), and anhydrous dichloromethane (4 mL) at rt under N2. After 20 h, the reaction was concentrated and purified by silica gel chromatography (1:0→7:3; hexanes:ethyl acetate) to give 8-(cyclopentyloxy)-7-methoxy-2-oxo-2H-chromen-4-yl 4-methylbenzenesulfonate: MS (ESI): 431.3.

Workup

  1. concentrationthe reaction was concentrated
  2. custompurified by silica gel chromatography (1:0→7:3; hexanes:ethyl acetate)

Sources & evidence

ORD record
ord-5723064d63964d548591af3a350eda5e
Source dataset
uspto-grants-2010_06
Patent number
US07745646B2

Linked notes

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