588702-95-8 → HCID 22481692, compound

HRID 2181665Notes

Reaction equation

HRID 2181665 reaction equation
[CH:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:6]=2[CH:7]=1)=[O:2].[CH3:16][Mg]Br>C1COCC1>[OH:2][CH:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([C:12]([O:14][CH3:15])=[O:13])[CH:9]=[CH:8][C:6]=2[CH:7]=1)[CH3:16]

Participants

4

Reactant 2

HCID 22481722588702-95-8HCID 178418573HCID 178418573, compound

Product 1

HCID 22481692HCID 22481692, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 2-formyl-1-benzofuran-6-carboxylate (750 mg, 3.67 mmol) is dissolved in anhydrous THF (30 ml) in a dry flask under nitrogen and cooled to 0° C. Methyl magnesium bromide (2.6 ml, 3.67 mmol) is added via syringe, and the reaction is stirred overnight, allowing the ice bath to expire. The reaction is quenched with 5% HCl (70 ml) and extracted with CH2Cl2 (3×25 ml). The combined organics are dried (MgSO4), filtered, and concentrated to a yellow oil. The crude material is chromatographed over 100 g slurry-packed silica gel, eluting with 35% EtOAc/hexane. The appropriate fractions are collected and concentrated to afford 412 mg (51%) of methyl 2-(1-hydroxyethyl)-1-benzofuran-6-carboxylate as a yellow oil that solidified upon standing. MS for C12H12O4, (EI) m/z: 220 (M)+.

Workup

  1. customThe reaction is quenched with 5% HCl (70 ml)
  2. extractionextracted with CH2Cl2 (3×25 ml)
  3. dry with materialThe combined organics are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to a yellow oil
  6. customThe crude material is chromatographed over 100 g slurry-packed silica gel
  7. washeluting with 35% EtOAc/hexane
  8. customThe appropriate fractions are collected
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-3b5292d9ed2f490c9852c53bf5615e0b
Source dataset
uspto-grants-2005_05
Patent number
US06894042B2

Reaction notes

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