Benzo(B)Thiophene → HCID 21477088, compound

HRID 2293694Notes

Reaction equation

HRID 2293694 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[CH:7][CH:8]=[CH:9][C:2]1=2.C([Li])CCC.[CH2:15]1[CH2:19][O:18][CH2:17][CH2:16]1>>[CH:15]1([CH:19]([C:5]2[S:1][C:2]3[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=3[CH:4]=2)[OH:18])[CH2:16][CH2:17]1

Participants

4

Reactant 3

HCID 7221Benzo(B)ThiopheneHCID 8028TetrahydrofuranHCID 178418339Butyllithium

Product 1

HCID 21477088HCID 21477088, compound

Conditions

Temperature
-78 °C

Procedure

Benzo[b]thiophene of formula II-1 (2.68 g) is added to THF (70 mL) and cooled to -78° C. n-Butyl lithium (1M in hexane, 20 mmol) is then added and the resulting solution stirred for 1.5 hours. The cooling bath is removed for 30 minutes and then cooled back to -78° C. Cyclopropylcarboxaldehyde (1.4 g) is then added in a single portion and the reaction quenched by adding a saturated NH4Cl solution. The reaction is extracted with ether, dried and solvent removed in vacuo to yield the title product as a clear oil that solidified on standing.

Workup

  1. additionis then added
  2. customThe cooling bath is removed for 30 minutes
  3. additionCyclopropylcarboxaldehyde (1.4 g) is then added in a single portion
  4. customthe reaction quenched
  5. additionby adding a saturated NH4Cl solution
  6. extractionThe reaction is extracted with ether
  7. customdried
  8. customsolvent removed in vacuo

Sources & evidence

ORD record
ord-00efb58c977b44d8804e3a5821151013
Source dataset
uspto-grants-1997_11
Patent number
US05686486

Reaction notes

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