Hydrochloric Acid → HCID 18989161, compound

HRID 2395554Notes

Reaction equation

HRID 2395554 reaction equation
Cl[C:2]1[C:10]2[C:9]([O:11][CH3:12])=[CH:8][S:7][C:6]=2[CH:5]=[CH:4][C:3]=1[C:13]([O:15]C)=O.[H-].[Na+].[CH3:19][C:20]([CH:22]1[CH2:24][CH2:23]1)=[O:21].Cl.[O:26]1CCC[CH2:27]1>O.C(O)(C)C>[CH:22]1([C:20](=[O:21])[CH2:19][C:13]([C:3]2[CH:4]=[CH:5][C:6]3[S:7][CH:8]=[C:9]([O:11][CH3:12])[C:10]=3[C:2]=2[O:26][CH3:27])=[O:15])[CH2:24][CH2:23]1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 13004Cyclopropyl methyl ketoneHCID 24758Sodium hydrideHCID 18989147HCID 18989147, compound

Product 1

HCID 18989161HCID 18989161, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Procedure

A solution of methyl 4-chloro-3-methoxybenzo[b]thiophene-5-carboxylate (3.95 g) in dry tetrahydrofuran was added to sodium hydride (60%, 1.355 g) and stirred under an inert atmosphere with warming to 50°-60° C. Cyclopropyl methyl ketone (2.59 g) was added with stirring at 50°-60° C. for 3 hours. After this time the reaction exothermed and was heated at 50°-60° C. for a further 1.5 hours. After cooling, isopropanol (5 ml) was cautiously added, followed by water (5 ml). The mixture was poured onto 2N hydrochloric acid and extracted with ether. The ether extracts were dried over anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by column chromatography on silica gel, eluting with ether/cyclohexane to yield 5-(3-cyclopropyl-1,3-dioxoprop-1-yl)-3,4-dimethoxybenzo[b]thiophene as a yellow solid (1.47 g), m.p. 77.5°-80° C.

Workup

  1. temperaturewith warming to 50°-60° C
  2. stirringwith stirring at 50°-60° C. for 3 hours
  3. customAfter this time the reaction exothermed
  4. temperaturewas heated at 50°-60° C. for a further 1.5 hours
  5. temperatureAfter cooling
  6. extractionextracted with ether
  7. dry with materialThe ether extracts were dried over anhydrous magnesium sulphate
  8. customevaporated in vacuo
  9. customThe residue was purified by column chromatography on silica gel
  10. washeluting with ether/cyclohexane

Sources & evidence

ORD record
ord-86bd72f19b6f46e69e7b35a5e7bab442
Source dataset
uspto-grants-1996_02
Patent number
US05489570

Reaction notes

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