Methane → 7-(3-[4-Acetyl-3-hydroxy-2-n-propylphenoxy]-2-hydroxypropoxy)-4-hydroxycoumarin

HRID 2050165Notes

Reaction equation

HRID 2050165 reaction equation
[C:1]([C:4]1[CH:34]=[CH:33][C:7]([O:8][CH2:9][CH:10]([OH:32])[CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17]([O:24]CC4C=CC=CC=4)=[CH:18][C:19](=[O:23])[O:20]3)=[CH:15][CH:14]=2)=[C:6]([CH2:35][CH2:36][CH3:37])[C:5]=1[OH:38])(=[O:3])[CH3:2].C>CN(C=O)C>[C:1]([C:4]1[CH:34]=[CH:33][C:7]([O:8][CH2:9][CH:10]([OH:32])[CH2:11][O:12][C:13]2[CH:22]=[C:21]3[C:16]([C:17]([OH:24])=[CH:18][C:19](=[O:23])[O:20]3)=[CH:15][CH:14]=2)=[C:6]([CH2:35][CH2:36][CH3:37])[C:5]=1[OH:38])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 297MethaneHCID 203314247-(3-[4-Acetyl-3-hydroxy-2-n-propylphenoxy]-2-hydroxypropoxy)-4-benzyloxycoumarin

Product 1

HCID 546860317-(3-[4-Acetyl-3-hydroxy-2-n-propylphenoxy]-2-hydroxypropoxy)-4-hydroxycoumarin

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Hydrogenation of 7-(3-[4-acetyl-3-hydroxy-2-n-propylphenoxy]-2-hydroxypropoxy)-4-benzyloxycoumarin (3.42 g; 0.0066 mole) in DMF (60 ml) at atmospheric pressure using 10% palladinized charcoal afforded the title compound; 2.86 g as a tlc pure foam. (DMSO); 9.13 (3H, t, J 6.7 Hz); 8.59 (2H, m) 7.40 (3H, s); 7.40 (2H, m); 6.30 (1H, broad exchangeable); 5.75 (5H, s); 4.75 (1H, broad exchangeable); 4.50 (1H, exchangeble) 3.30 (1H, d, J 9.3Hz); 3.01 (2H, m); 2.23 (1H, d, J 9.6 Hz); 2.15 (1H, d, J 9.3Hz); 1 low field sharp exchangeable. Molecular ion at m/e 428.

Sources & evidence

ORD record
ord-e873d07312384e69b73405c9d15e4443
Source dataset
uspto-grants-1980_04
Patent number
US04200577

Reaction notes

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