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

HRID 29337

反応式

HRID 29337 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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)+.

後処理

  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)

出典と根拠

ORDレコード
ord-965edae8814849798c651b63a638beac
出典データセット
uspto-grants-2008_09
特許番号
US07420001B2

関連ノート

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