Ethylene Glycol → HCID 24896967, compound

HRID 1819884Notes

Reaction equation

HRID 1819884 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:9]2[O:10][C:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:8]=2[CH:7]=1)=[O:4].[CH2:20]([OH:23])[CH2:21][OH:22].CC(C)([O-])C.[K+]>CN(C)C=O>[OH:22][CH2:21][CH2:20][O:23][CH2:2][C:3]([NH:5][C:6]1[CH:19]=[CH:18][C:9]2[O:10][C:11]3[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:8]=2[CH:7]=1)=[O:4]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 23665647Potassium tert-butoxideHCID 24900205HCID 24900205, compound

Product 1

HCID 24896967HCID 24896967, compoundYield 11.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure of Example 40, 2-chloro-N-7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylacetamide (0.13 g, 0.45 mmol), ethylene glycol (0.031 mL, 0.56 mmol), and potassium tert-butoxide (0.10 g, 0.90 mmol) in dimethylformamide (5 m L) provided 2-(2-hydroxyethoxy)-N-7,8,9,10-tetrahydro-6H-benzo[b]cyclohepta[d]furan-2-ylacetamide (0.016 g) after reverse-phase HPLC purification. MS (ESI) m/z 304 ([M+H]+); MS (ESI) m/z 302 ([M−H]−).

Sources & evidence

ORD record
ord-6db1ad67161d4bfb8a2604a2e24fd173
Source dataset
uspto-grants-2009_10
Patent number
US07601856B2

Reaction notes

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