Water → Ethyl 4-(2-hydroxyethyl)-3-methyl-1-benzofuran-2-carboxylate

HRID 29337

Reaction equation

HRID 29337 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[O:7][C:8]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]=[CH2:17])[C:9]=2[C:10]=1[CH3:11])=[O:5])[CH3:2].B.C1C[O:22]CC1.O.C([O-])([O-])=O.C([O-])([O-])=O.OO.OO.OO.[Na+].[Na+].[Na+].[Na+]>C1COCC1>[OH:22][CH2:17][CH2:16][C:12]1[C:9]2[C:10]([CH3:11])=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[O:7][C:8]=2[CH:15]=[CH:14][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 159762Sodium percarbonateHCID 2723981Borane;tetrahydrofuranHCID 687131603-Methyl-4-vinylbenzofuran-2-carboxylic acid ethyl ester

Product 1

HCID 68711735Ethyl 4-(2-hydroxyethyl)-3-methyl-1-benzofuran-2-carboxylateYield 80.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.35 g (1.5 mmol) of 3-methyl-4-vinyl-1-benzofuran-2-carboxylate (Example 87, Step 1) in 3 mL of THF, cooled in an ice bath, was added 1 mL (1 mmol) of borane-THF complex (1.0M solution in THF). The reaction was stirred at room temperature for 2 hours. The reaction was cooled in an ice bath and 1.5 mL of water was added. Next 0.61 g of sodium percarbonate was added in one portion. The reaction was heated at ˜50° C. for 1 hour, then cooled to room temperature. Water was added and the resulting mixture was extracted with ethyl acetate. The organic layer washed with water and brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was chromatographed on silica gel eluting with hexane/ethyl acetate (2:1) to provide 0.20 g of ethyl 4-(2-hydroxyethyl)-3-methyl-1-benzofuran-2-carboxylate. Yield 54%. m.p. 88-90° C.; MS 249.1 (M+H)+.

Workup

  1. temperatureThe reaction was cooled in an ice bath
  2. temperatureThe reaction was heated at ˜50° C. for 1 hour
  3. temperaturecooled to room temperature
  4. extractionthe resulting mixture was extracted with ethyl acetate
  5. washThe organic layer washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was chromatographed on silica gel eluting with hexane/ethyl acetate (2:1)

Sources & evidence

ORD record
ord-965edae8814849798c651b63a638beac
Source dataset
uspto-grants-2008_09
Patent number
US07420001B2

Linked notes

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