Hydrochloric Acid → HCID 22728980, compound

HRID 2085128Notes

Reaction equation

HRID 2085128 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]2[CH:12]=[CH:11][S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.C([Li])CCC.[OH2:19].Cl.C1[CH2:25][O:24]CC1>CCCCCC>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:13]2[CH:12]=[C:11]([C:25]([OH:24])=[O:19])[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028TetrahydrofuranHCID 22729028HCID 22729028, compoundHCID 178418339Butyllithium

Product 1

HCID 22728980HCID 22728980, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

4-(Methoxymethyloxy)benzo(b)thiophene (83 g) was dissolved in THF (700 ml) and the mixture was cooled to −78° C. At this temperature, a solution (363 ml) of n-butyllithium in hexane was added dropwise. The temperature was raised to 0° C. and then cooled again to −35° C., and carbon dioxide was bubbled. After the completion of the reaction, the reaction mixture was poured into water, and in the presence of ice, hydrochloric acid was added to adjust its pH to 1 and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and after filtration, the solvent was evaporated under reduced pressure to give the title compound (80 g).

Workup

  1. temperatureThe temperature was raised to 0° C.
  2. temperaturecooled again to −35° C.
  3. customcarbon dioxide was bubbled
  4. customAfter the completion of the reaction
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationafter filtration
  8. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-455b6d132ec341c5b15e360439f86e11
Source dataset
uspto-grants-2004_04
Patent number
US06720320B2

Reaction notes

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