Hydrochloric Acid → 3-Methyl-5-(tributylstannyl)thiophene-2-carbaldehyde

HRID 9657

Reaction equation

HRID 9657 reaction equation
[CH2:1]([Sn:5]([CH2:21][CH2:22][CH2:23][CH3:24])([CH2:17][CH2:18][CH2:19][CH3:20])[C:6]1[S:7][C:8]([CH:12]2OCC[O:13]2)=[C:9]([CH3:11])[CH:10]=1)[CH2:2][CH2:3][CH3:4].Cl>O1CCCC1>[CH3:11][C:9]1[CH:10]=[C:6]([Sn:5]([CH2:17][CH2:18][CH2:19][CH3:20])([CH2:21][CH2:22][CH2:23][CH3:24])[CH2:1][CH2:2][CH2:3][CH3:4])[S:7][C:8]=1[CH:12]=[O:13]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21986287Tributyl[5-(1,3-dioxolan-2-yl)4-methylthien-2-yl]stannane2×

Product 1

HCID 219863013-Methyl-5-(tributylstannyl)thiophene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of tributyl[5-(1,3-dioxolan-2-yl)4-methylthien-2-yl]stannane (intermediate 76, 2.92 g), 1M aqueous hydrochloric acid (3 ml) and tetrahydrofuran (10 ml) was stirred at reflux for 30 minutes. The reaction mixture was cooled, extracted thrice with diethylether. The organic solutions were combined, extracted with saturated sodium bicarbonate and dried with brine and over magnesium sulfate. The product isolated after evaporation of the solvent was further purified by flash column chromatography using cyclohexane:ethyl acetate (50:1) as eluent to give the title compound as a yellow oil.

Workup

  1. temperatureat reflux for 30 minutes
  2. temperatureThe reaction mixture was cooled
  3. extractionextracted thrice with diethylether
  4. extractionextracted with saturated sodium bicarbonate
  5. dry with materialdried with brine and over magnesium sulfate
  6. customThe product isolated
  7. customafter evaporation of the solvent
  8. customwas further purified by flash column chromatography

Sources & evidence

ORD record
ord-c4e70ab5a3954c6f92ec92114990c273
Source dataset
uspto-grants-2006_08
Patent number
US07091237B2

Linked notes

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