Benzo(B)Thiophene → HCID 5061934, compound

HRID 2351462Notes

Reaction equation

HRID 2351462 reaction equation
[C:1]([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH:5]=1)(=O)[CH3:2].S1C=CC2C=CC=CC1=2.C([Li])CCC.C[N:28]([C:31](=[O:33])[CH3:32])[O:29]C>C1COCC1>[OH:29][N:28]([CH:1]([C:4]1[S:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[CH:5]=1)[CH3:2])[C:31](=[O:33])[CH3:32]

Participants

6

Reactant 4

HCID 7221Benzo(B)ThiopheneHCID 898052-Acetylbenzo[b]thiopheneHCID 537505N-Methoxy-N-methylacetamideHCID 178418339Butyllithium

Product 1

HCID 5061934HCID 5061934, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

2-Acetyl benzo[b]thiophene. Method a. Using the method described in Scheme 1, benzo[b]thiophene (10 g, 75 mmole) was dissolved in THF (50 mL) and cooled to -78° C. Butyl lithium (28 mL, 2.7 M in hexanes) was added. The mixture was stirred for 15 minutes and N,O-dimethyl acetohydroxamic acid was added. Following an additional 30 minutes of stirring, the reaction was quenched at -78° C. with ethanol and 2N HC1 solution and extracted into ether. The solvent was removed in vacuo and the residue chromatographed on silica gel eluting with 20% ether in pentane to yield 6.9 g of the desired product as a white solid.

Workup

  1. waitFollowing an additional 30 minutes
  2. stirringof stirring
  3. customthe reaction was quenched at -78° C. with ethanol and 2N HC1 solution
  4. extractionextracted into ether
  5. customThe solvent was removed in vacuo
  6. customthe residue chromatographed on silica gel eluting with 20% ether in pentane

Sources & evidence

ORD record
ord-45c8109020cf41e38d2e370e7965705b
Source dataset
uspto-grants-1989_10
Patent number
US04873259

Reaction notes

Loading…