Hydrochloric Acid → 3-(3-(Carbomethoxy)propionyloxy)-2,5-diphenylthiophene

HRID 359147Notes

Reaction equation

HRID 359147 reaction equation
[C:1]1([C:7]2[S:8][C:9]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:11]=2[OH:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:19]([CH2:23][CH2:24][C:25](Cl)=[O:26])([O:21][CH3:22])=[O:20].CCOCC.Cl>N1C=CC=CC=1.O>[C:19]([CH2:23][CH2:24][C:25]([O:12][C:11]1[CH:10]=[C:9]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[S:8][C:7]=1[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:26])([O:21][CH3:22])=[O:20]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 73888Butanoic acid, 4-chloro-4-oxo-, methyl esterHCID 150787382,5-Diphenylthiophene-3-ol

Product 1

HCID 150787393-(3-(Carbomethoxy)propionyloxy)-2,5-diphenylthiophene

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

To a stirred, ice-cooled solution of 2,5-diphenyl-3-hydroxythiophene (0.12 g, 0.5 mmol) in dried pyridine (5.0 ml) under a nitrogen atmosphere was added 3-carbomethoxypropionyl chloride (0.1 g, 0.66 mmol) over ca. 20 seconds. The mixture was allowed to stir cold for 15 minutes and then at ambient temperatures for 4 hours. The mixture was added in portions to a stirred mixture of ether, ice, water, and 2N hydrochloric acid (40 ml), the ether layer washed 2 times with water, dried over sodium sulfate, filtered and concentrated to 0.18 g of oily (I). M.S.: M+ =366; NMR: consistent. ##STR26##

Workup

  1. waitat ambient temperatures for 4 hours
  2. washthe ether layer washed 2 times with water
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated to 0.18 g of oily (I)

Sources & evidence

ORD record
ord-60c775b71298495a9f7a20b6340f093b
Source dataset
uspto-grants-1991_03
Patent number
US04999436

Reaction notes

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