1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-Fluoro-7-methoxy-1-benzothiophene

HRID 2220341Notes

Reaction equation

HRID 2220341 reaction equation
[F:1][C:2]1[C:7]2[CH:8]=[C:9](C(O)=O)[S:10][C:6]=2[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1.C1CCN2C(=NCCC2)CC1>CC(N(C)C)=O>[F:1][C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[C:5]([O:14][CH3:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 235689524-Fluoro-7-methoxy-1-benzothiophene-2-carboxylic acid

Product 1

HCID 221712354-Fluoro-7-methoxy-1-benzothiopheneYield 70%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

4-Fluoro-7-methoxy-1-benzothiophene-2-carboxylic acid (2.00 g, 8.84 mmol) was added in one portion to DBU (8 mL) and dimethyl acetamide (10 mL). This was heated in the microwave with 300W at 200° C. for 1 h. The reaction mixture was allowed to cool and poured onto water (100 mL). Product was extracted with hexane (2×100 mL), washed with aqueous hydrochloric acid (2 N, 50 mL), aqueous sodium hydroxide (2 N, 50 mL), and the combined organic extracts were dried (MgSO4) and concentrated in vacuo. The residue was purified by flash chromatography eluting silica gel with hexane:ethyl acetate [96:4] to give an oil (1.12 g, 70%): δH (300 MHz, CDCl3) 7.4 (2H, s, Ar), 6.9 (1H, t, Ar), 6.60 (1H, dd, Ar), 3.91 (3H, s, OCH3).

Workup

  1. temperatureto cool
  2. additionpoured onto water (100 mL)
  3. extractionProduct was extracted with hexane (2×100 mL)
  4. washwashed with aqueous hydrochloric acid (2 N, 50 mL), aqueous sodium hydroxide (2 N, 50 mL)
  5. dry with materialthe combined organic extracts were dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting silica gel with hexane

Sources & evidence

ORD record
ord-2383979560754687a326341e60ca070d
Source dataset
uspto-grants-2008_08
Patent number
US07417064B2

Reaction notes

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