Water → HCID 67484700, compound

HRID 2233359Notes

Reaction equation

HRID 2233359 reaction equation
[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]([OH:15])[C:5]=2[CH:6]=1.C(=O)([O-])[O-].[K+].[K+].I[CH2:23][CH:24]([CH3:26])[CH3:25].O>CN(C=O)C>[CH3:1][C:2]1[O:3][C:4]2[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]([O:15][CH2:23][CH:24]([CH3:26])[CH3:25])[C:5]=2[CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10556Isobutyl iodideHCID 11430Potassium CarbonateHCID 46941595Methyl 4-hydroxy-2-methyl-1-benzofuran-6-carboxylate

Product 1

HCID 67484700HCID 67484700, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

2-Methyl-4-hydroxy-6-methoxycarbonylbenzofuran (Method 12; 412 mg, assumed 1.0 mmol) was stirred in anhydrous DMF (10 ml) and the solution treated sequentially with potassium carbonate (690 mg, 5 mmol, 5 eq) and 1-iodo-2-methylpropane (442 mg, 276 μl, 2.4 mmol, 2.4 eq). The reaction mixture was stirred at 90° C. for 3 hours, then cooled and poured into water; the resulting mixture was extracted twice with ethyl acetate, the extracts dried (MgSO4) and evaporated in vacuo to yield a brown oil. This was chromatographed (50 g Bondelut, eluting with hexane containing ethyl acetate, 0-100%) to give the title compound as a clear oil contaminated with ca 15% of the corresponding iso-butyl ester. NMR: 1.02 (d, 6H), 2.06 (sept, 1H), 2.45 (s, 3H), 3.84 (s, 3H), 3.91 (d, 2H), 6.66 (s, 1H), 7.24 (s, 1H), 7.66 (s, 1H); the spectrum also contained signals consistent with isobutyl ester, ca 15 mol %.

Workup

  1. temperaturecooled
  2. extractionthe resulting mixture was extracted twice with ethyl acetate
  3. dry with materialthe extracts dried (MgSO4)
  4. customevaporated in vacuo
  5. customto yield a brown oil
  6. customThis was chromatographed
  7. wash(50 g Bondelut, eluting with hexane containing ethyl acetate, 0-100%)

Sources & evidence

ORD record
ord-0115664dfbbf4993845100299f4b2766
Source dataset
uspto-grants-2010_05
Patent number
US07709505B2

Reaction notes

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