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Hydrochloric Acid → 5-(2-Ethyl-[1,3]dioxolan-2-yl)thiophene-2-carbaldehyde

HRID 49327
Notes
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Reaction equation

HRID 49327 reaction equation
[CH2:1]([C:3]1([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)[O:7][CH2:6][CH2:5][O:4]1)[CH3:2].C([Li])(C)(C)C.CN([CH:21]=[O:22])C.Cl>C1COCC1>[CH2:1]([C:3]1([C:8]2[S:9][C:10]([CH:21]=[O:22])=[CH:11][CH:12]=2)[O:4][CH2:5][CH2:6][O:7]1)[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 179347502-Ethyl-2-2-thienyl-[1,3]dioxolaneHCID 178418306HCID 178418306, compound

Product 1

HCID 179347875-(2-Ethyl-[1,3]dioxolan-2-yl)thiophene-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

Conditions

Temperature
-78 °C

Procedure

15 g (81.4 mmol) of 2-ethyl-2-2-thienyl-[1,3]dioxolane are dissolved in 300 mL of anhydrous THF and the mixture is then cooled to −78° C. 53 mL (89 mmol) of 1.7 M tert-butyllithium solution are then added, after which the reaction medium is stirred for 1 hour. 10 mL (120 mmol) of anhydrous DMF are then added and the medium is stirred for 1 hour. The reaction medium is treated at −78° C. with 1N hydrochloric acid solution and is then extracted with ethyl acetate and the organic phases are combined, dried and concentrated under reduced pressure. The residue obtained is purified by chromatography on a column of silica. A yellow oil is obtained (m=19 g; Y=100%).

Workup

  1. stirringthe medium is stirred for 1 hour
  2. extractionis then extracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue obtained
  6. customis purified by chromatography on a column of silica
  7. customA yellow oil is obtained (m=19 g; Y=100%)

Sources & evidence

ORD record
ord-b5d2b8c3abe54f9aab4ed54ff59fd55d
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06706725B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes