Potassium Carbonate → N-[6-(3-Ethoxypropoxy)-2,2-dimethylchroman-4-yl]-N-(2-methoxyethyl)methanesulfonamide

HRID 567072Notes

Reaction equation

HRID 567072 reaction equation
[CH3:1][C:2]1([CH3:22])[CH2:11][CH:10]([N:12]([CH2:17][CH2:18][O:19][CH3:20])[S:13]([CH3:16])(=[O:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:21])[CH:8]=2)[O:3]1.C(=O)([O-])[O-].[K+].[K+].[CH2:29]([O:31][CH2:32][CH2:33][CH2:34]Br)[CH3:30]>CCCCCCC.CC(=O)OCC>[CH2:29]([O:31][CH2:32][CH2:33][CH2:34][O:21][C:7]1[CH:8]=[C:9]2[C:4](=[CH:5][CH:6]=1)[O:3][C:2]([CH3:22])([CH3:1])[CH2:11][CH:10]2[N:12]([CH2:17][CH2:18][O:19][CH3:20])[S:13]([CH3:16])(=[O:15])=[O:14])[CH3:30]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2604931-bromo-3-ethoxypropaneHCID 17786848N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-(2-methoxyethyl)methanesulfonamide

Product 1

HCID 9866555N-[6-(3-Ethoxypropoxy)-2,2-dimethylchroman-4-yl]-N-(2-methoxyethyl)methanesulfonamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

0.5 g (1.5 mmol) of N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-(2-methoxyethyl)methanesulfonamide (Example 16b) was reacted with potassium carbonate and 3-ethoxy-1-bromopropane analogously to Example 1g. After column chromatography on silica gel using n-heptane/EA (5:1), 0.35 g of oily product was obtained.

Sources & evidence

ORD record
ord-6c0ee2ab4c9c4e39be2ec6ec07a998b8
Source dataset
uspto-grants-2001_01
Patent number
US06177449B1

Reaction notes

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