Potassium Carbonate → 1-Tert-butyl 7-ethyl 2-[(methylthio)acetyl]heptanedioate

HRID 860425ノート

反応式

HRID 860425 の反応式
[CH3:1][S:2][CH2:3][C:4](=[O:13])[CH2:5][C:6]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])=[O:7].C(=O)([O-])[O-].[K+].[K+].I[CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C)C=O>[CH3:1][S:2][CH2:3][C:4]([CH:5]([CH2:21][CH2:22][CH2:23][CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:6]([O:8][C:9]([CH3:10])([CH3:12])[CH3:11])=[O:7])=[O:13]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 4169827Ethyl 5-iodopentanoateHCID 57444537Tert-butyl 4-(methylthio)-3-oxobutanoate

生成物 1

HCID 574813391-Tert-butyl 7-ethyl 2-[(methylthio)acetyl]heptanedioate収率 72.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of tert-butyl 4-(methylthio)-3-oxobutanoate (5.00 g) and potassium carbonate (3.72 g) in dimethylformamide (25 mL) was added ethyl 5-iodopentanoate (6.89 g) and the mixture was stirred at ambient temperature for 15 hours. The mixture was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and brine, dried over magnesium sulfate, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (20:1-10:1) to give 1-tert-butyl 7-ethyl 2-[(methylthio)acetyl]heptanedioate as colorless oil (5.88 g).

後処理

  1. customThe mixture was partitioned between ethyl acetate and water
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a mixture of hexane and ethyl acetate (20:1-10:1)

出典と根拠

ORDレコード
ord-67d7276d9f49414e83f8e109d4167b3d
出典データセット
uspto-grants-2006_12
特許番号
US07153854B2

反応ノート

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