Dichloromethane → HCID 13745628, compound

HRID 986711Notes

Reaction equation

HRID 986711 reaction equation
[C:1]([C:4]1[CH:24]=[CH:23][C:7]([O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=2[F:22])=[C:6]([CH2:25][CH2:26][CH3:27])[C:5]=1[OH:28])(=[O:3])[CH3:2].ClCCl.C(N(CC)CC)C.[C:39](OC(=O)C)(=[O:41])[CH3:40]>CN(C)C1C=CN=CC=1.CO>[C:39]([O:28][C:5]1[C:6]([CH2:25][CH2:26][CH3:27])=[C:7]([CH:23]=[CH:24][C:4]=1[C:1](=[O:3])[CH3:2])[O:8][CH2:9][CH2:10][CH2:11][O:12][C:13]1[CH:21]=[CH:20][C:16]([C:17]([OH:19])=[O:18])=[CH:15][C:14]=1[F:22])(=[O:41])[CH3:40]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 13745623HCID 13745623, compound

Product 1

HCID 13745628HCID 13745628, compound

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-[3-(4-acetyl-3-hydroxy-2-propylphenoxy)propoxy]-3-fluorobenzoic acid (700 mg), dichloromethane (25 ml), triethylamine (2ml), acetic anhydride (2ml) and 4-dimethylaminopyridine (catalytic amount) was stirred at ice-cooling to room temperature for 6.5 hours. To the reaction mixture was added methanol (2ml), and the mixture was stirred for 30 minutes. After concentration, water was added to the residue. Solid materials were recovered by filtration and subjected to recrystallization from aqueous methanol to give crystals of 4-[3-(3-acetoxy-4-acetyl-2-propylphenoxy)propoxy]-3-fluorobenzoic acid (723 mg). m.p. 144°-145° C.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. concentrationAfter concentration, water
  3. additionwas added to the residue
  4. filtrationSolid materials were recovered by filtration
  5. customsubjected to recrystallization from aqueous methanol

Sources & evidence

ORD record
ord-707980c8c2ec48f08bc4c32c0c936e17
Source dataset
uspto-grants-1987_12
Patent number
US04714774

Reaction notes

Loading…