Potassium Carbonate → 2-Ethynyl-6-methoxybenzofuran

HRID 710333Notes

Reaction equation

HRID 710333 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[CH:12][C:6]2[CH:7]=[C:8]([CH:10]=O)[O:9][C:5]=2[CH:4]=1.[CH3:14]OP(C(=[N+]=[N-])C(=O)C)(=O)OC.C([O-])([O-])=O.[K+].[K+]>CO>[C:10]([C:8]1[O:9][C:5]2[CH:4]=[C:3]([O:2][CH3:1])[CH:13]=[CH:12][C:6]=2[CH:7]=1)#[CH:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 409082-Benzofurancarboxaldehyde, 6-methoxy-HCID 136023029(1E)-1-diazo-1-dimethoxyphosphorylpropan-2-one

Product 1

HCID 717417602-Ethynyl-6-methoxybenzofuranYield 88%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 6-methoxybenzofuran-2-carbaldehyde (0.21 g, 1.19 mmol), dimethyl(1-diazo-2-oxopropyl)phosphonate (0.27 g, 1.43 mmol) and K2CO3 (0.33 g, 2.4 mmol) in anhydrous MeOH (5 ml) was stirred overnight at room temperature. The solvent was evaporated and the residue was taken in EtOAc (50 ml), washed with H2O and dried over MgSO4 and filtered. The filtrate was evaporated to dryness to give the crude product (0.18 g; 88%), which was used in the next step without purification. 1H-NMR (CDCl3) 1.53 (s, 1H); 3.82 (s, 3H); 6.87 (dd, 1H, J=2.25, 8.58 Hz), 6.92 (s, 1H); 6.95 (d, 1H, J=2.01 Hz); 7.39 (d, 1H, J=8.61 Hz).

Workup

  1. customThe solvent was evaporated
  2. washwashed with H2O
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-9e8d91bc9d044be6ba02e03ed6cf7097
Source dataset
uspto-grants-2015_11
Patent number
US09181182B2

Reaction notes

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