Hydrochloric Acid → HCID 13888631, compound

HRID 629165Notes

Reaction equation

HRID 629165 reaction equation
Br[C:2]1[S:3][C:4]([CH2:7][O:8][CH3:9])=[CH:5][CH:6]=1.C([Li])CCC.CN(C)[CH:17]=[O:18].Cl>O1CCCC1.CN(C)P(N(C)C)(N(C)C)=O>[CH3:9][O:8][CH2:7][C:4]1[S:3][C:2]([CH:17]=[O:18])=[CH:6][CH:5]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 13025550HCID 13025550, compoundHCID 178418339Butyllithium

Product 1

HCID 13888631HCID 13888631, compoundYield 31.1%

Reagents, catalysts & solvents 1

HCID 86583969tetrahydrofuran HMPASolvent

Conditions

Temperature
-78 °C

Procedure

To a solution of 2-bromo-5-(methoxymethyl)thiophene (439 mg, 2.12 mmol) in 6 mL of 9:1 tetrahydrofuran/hexamethylphosphoramide under argon at −78° C. was added n-butyllithium (0.93 mL, 2.5 M in hexanes) dropwise. After stirring for 2 minutes at −78° C., dimethylformamide (0.82 mL, 10.6 mmol) was added in a single portion and the reaction mixture was allowed to warm to room temperature before being poured into 30 mL of 1 N hydrochloric acid. Organics were extracted with 1:1 ether/hexanes (3×30 mL), washed with water (2×30 mL, brine (30 mL), dried over magnesium sulfate, filtered and concentrated. The crude residue was subjected to chromatography on silica gel with gradient elution (5-20% ethyl acetate in hexanes) to give 5-(methoxymethyl)thiophene-2-carbaldehyde (103 mg, 31%) as an oil. Used without further characterization.

Workup

  1. temperatureto warm to room temperature
  2. extractionOrganics were extracted with 1:1 ether/hexanes (3×30 mL)
  3. washwashed with water (2×30 mL, brine (30 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washThe crude residue was subjected to chromatography on silica gel with gradient elution (5-20% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-c4f0385284df4279a0d4347739bb5c17
Source dataset
uspto-grants-2016_04
Patent number
US09315495B2

Reaction notes

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