Potassium Carbonate → HCID 86700908, compound

HRID 625123Notes

Reaction equation

HRID 625123 reaction equation
[Cl:1][C:2]1[CH:13]=[C:12]([OH:14])[C:5]2[CH:6]=[C:7]([C:9](=[O:11])[CH3:10])[O:8][C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:6]([O:14][C:12]1[C:5]2[CH:6]=[C:7]([C:9](=[O:11])[CH3:10])[O:8][C:4]=2[CH:3]=[C:2]([Cl:1])[CH:13]=1)[C:5]1[CH:12]=[CH:13][CH:2]=[CH:3][CH:4]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 86700907HCID 86700907, compound

Product 1

HCID 86700908HCID 86700908, compoundYield 186.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A stirred solution of 1-(6-chloro-4-hydroxybenzofuran-2-yl)ethanone (Example 37D, 1.18 g, 5.60 mmol) in dry DMF (10 mL, 129 mmol) at r.t. was charged with K2CO3 (0.774 g, 5.60 mmol) and DMF. The reaction mixture was stirred for 1.5 hours then partitioned between ethyl acetate and water. The organic phase was washed with brine, dried (MgSO4), filtered and concentrated to dryness. The residue was purified by ISCO using hexanes/EtOAc as eluent. Fractions containing the desired product were concentrated to give the title material (1.57 g, 5.22 mmol, 93% yield) as an amber colored oil. LC (Method B): 2.420 min. LCMS (APCI) calcd for C17H14ClO3 [M+H]+ m/z 301.06, found 301.0. 1H NMR (CDCl3, 400 MHz) δ ppm: 8.00 (d, J=0.8 Hz, 1H), 7.53 (m, 3H), 7.44 (m, 2H), 7.38 (m, 1H), 7.10 (d, J=1.6 Hz, 1H), 5.53 (s, 2H), 2.54 (s, 3H).

Workup

  1. customthen partitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was purified by ISCO
  7. additionFractions containing the desired product
  8. concentrationwere concentrated

Sources & evidence

ORD record
ord-e9d1ee6bb05041ec81efc36ac78d100c
Source dataset
uspto-grants-2016_04
Patent number
US09303065B2

Reaction notes

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