Solketal → HCID 53682346, compound

HRID 1200054Notes

Reaction equation

HRID 1200054 reaction equation
[S:1]1[CH:5]=[C:4]([CH:6]=[CH:7][C:8]2[S:12][C:11]([C:13](Cl)=[O:14])=[CH:10][CH:9]=2)[C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2.CC1(C)OC(CO)C[O:22]1>N1C=CC=CC=1>[S:1]1[CH:5]=[C:4]([CH:6]=[CH:7][C:8]2[S:12][C:11]([C:13]([OH:22])=[O:14])=[CH:10][CH:9]=2)[C:3]2[CH:16]=[CH:17][CH:18]=[CH:19][C:2]1=2

Participants

4

Reactant 2

HCID 7528SolketalHCID 539913705-[2-(Benzo[b]thiophen-3-yl)ethenyl]thiophene-2-carboxylic acid chloride

Product 1

HCID 53682346HCID 53682346, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The acid chloride of 5-[2-(benzo[b]thiophen-3-yl)ethenyl]thiophene-2-carboxylic acid was prepared as described in Example 9. To a solution of 5-[2-(benzo[b]thiophen-3-yl)ethenyl]thiophene-2-carboxylic acid chloride (5.0 g) and pyridine (50 ml) was added 2,2-dimethyl-1,3-dioxolane-4-methanol (2.17 g). After refluxing overnight, the mixture was evaporated. The residue was dissolved in ethyl acetate, filtered, and concentrated. The residue was purified by high performance liquid chromatography (silica gel, loaded and eluted in 2:1 ethyl acetate:hexane). The appropriate fractions were combined and evaporated. Trituration of the residue with hexane yielded 2.60 g (39%) of product, mp 77°-79° C.

Workup

  1. temperatureAfter refluxing overnight
  2. customthe mixture was evaporated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by high performance liquid chromatography (silica gel, loaded and eluted in 2:1 ethyl acetate:hexane)
  7. customevaporated

Sources & evidence

ORD record
ord-23c7f285a13a4ca1b52e29e9185b8772
Source dataset
uspto-grants-1990_02
Patent number
US04904674

Reaction notes

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