Benzo(B)Thiophene → HCID 15550519, compound

HRID 651480Notes

Reaction equation

HRID 651480 reaction equation
C([Li])CCC.[CH:6]1[CH:7]=[CH:8][C:9]2[S:14][CH:13]=[CH:12][C:10]=2[CH:11]=1.[CH3:15][C:16]1[CH:17]=[C:18]([CH:22]=[O:23])[O:19][C:20]=1[CH3:21]>C1COCC1>[S:14]1[C:13]([CH:22]([C:18]2[O:19][C:20]([CH3:21])=[C:16]([CH3:15])[CH:17]=2)[OH:23])=[CH:12][C:10]2[CH:11]=[CH:6][CH:7]=[CH:8][C:9]1=2

Participants

5

Reactant 3

HCID 7221Benzo(B)ThiopheneHCID 6434064,5-Dimethyl-2-furaldehydeHCID 178418339Butyllithium

Product 1

HCID 15550519HCID 15550519, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

n-Butyl lithium (2.5 N in hexanes, 32.2 mL, 80.5 mmol) was added to a stirred solution of thianaphthene (10.6 g, 78.9 mmol) in THF (290 mL) at −78° C. After 15 min., a solution of 4,5-dimethyl-2-furaldehyde (9.79 g, 78.9 mmol) in THF (10 mL) was added. After additional 1 hour, the reaction mixture was quenched with 10% aqueous ammonium chloride (150 mL) and further diluted with water (150 mL). Aqueous mixture was extracted with dichloromethane. The combined dichloromethane extracts were washed with water, dried with brine and anhydrous Na2SO4, and concentrated to provide the title compound as an yellow oil (20.84 g, 100%): NMR (DMSO-d6); δ 7.89 (d, J=8 Hz, 1H), 7.76 (d, J=8, Hz, 1H), 7.35-7.26 (m, 2H), 7.25 (s, 1H), 6.36 (s, 1H), 6.08 (s, 1H), 5.92 (s, 1H), 2.13 (s, 3H), 1.86 (s, 3H); MS (EI): [M+], 258.

Workup

  1. waitAfter additional 1 hour
  2. customthe reaction mixture was quenched with 10% aqueous ammonium chloride (150 mL)
  3. additionfurther diluted with water (150 mL)
  4. extractionAqueous mixture was extracted with dichloromethane
  5. washThe combined dichloromethane extracts were washed with water
  6. dry with materialdried with brine and anhydrous Na2SO4
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-eaa831828f134db8a0e82fc73b007e25
Source dataset
uspto-grants-2001_08
Patent number
US06281238B1

Reaction notes

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