Hydrochloric Acid → HCID 118222788, compound

HRID 629167Notes

Reaction equation

HRID 629167 reaction equation
[CH:1]([O:4][C:5]1[S:6][CH:7]=[CH:8][CH:9]=1)([CH3:3])[CH3:2].C([Li])CCC.CN(C)[CH:17]=[O:18].Cl>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[CH:1]([O:4][C:5]1[S:6][C:7]([CH:17]=[O:18])=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 230580572-[(Propan-2-yl)oxy]thiopheneHCID 178418339Butyllithium

Product 1

HCID 118222788HCID 118222788, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 86583969tetrahydrofuran HMPASolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-isopropoxythiophene (250 mg, 1.76 mmol) in 9 mL of 9:1 tetrahydrofuran/hexamethylphosphoramide under argon at −78° C. was added n-butyllithium (0.77 mL, 2.5 M in hexanes) dropwise. After stirring at −78° C. for 20 minutes, dimethylformamide (0.68 mL, 8.80 mmol) was added in a single portion and the reaction mixture allowed to warm to room temperature while stirring, before being poured into 30 mL of 1 N hydrochloric acid. Organics were extracted with 1:1 ether/hexanes (2×35 mL), washed with 1 N hydrochloric acid (2×20 mL), water (20 mL) and brine, dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel (7% ethyl acetate in hexanes) to give 5-isopropoxy-2-thiophenecarbaldehyde (108 mg, 36%). Used without further characterization.

Workup

  1. temperatureto warm to room temperature
  2. stirringwhile stirring
  3. extractionOrganics were extracted with 1:1 ether/hexanes (2×35 mL)
  4. washwashed with 1 N hydrochloric acid (2×20 mL), water (20 mL) and brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9fb3c7a1cc5a4cdb9bd5bb3b7cf439ca
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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