Sodium hydride → 1-Tert-butyl 5-ethyl 2-[(acetyloxy)acetyl]pentanedioate

HRID 2250635ノート

反応式

HRID 2250635 の反応式
[H-].[Na+].[C:3]([O:6][CH2:7][C:8](=[O:17])[CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])(=[O:5])[CH3:4].I[CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22]>C1COCC1>[C:3]([O:6][CH2:7][C:8]([CH:9]([CH2:19][CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[O:17])(=[O:5])[CH3:4]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 10911297Ethyl 3-iodopropanoateHCID 57260374Tert-butyl 4-(acetyloxy)-3-oxobutanoate

生成物 1

HCID 574813831-Tert-butyl 5-ethyl 2-[(acetyloxy)acetyl]pentanedioate収率 58.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a suspension of 60% NaH (1.02 g) in THF (50 mL) was added tert-butyl 4-(acetyloxy)-3-oxobutanoate (5.00 g) under ice-water cooling and the mixture was stirred at 0° C. for 0.5 hour. To this added ethyl 3-iodopropanoate (5.54 g) and the mixture was stirred at 50° C. for 8 hours. The mixture was partitioned between AcOEt and water. The organic layer was separated, washed with brine, dried over MgSO4, and evaporated in vacuo. The residue was purified by silica gel column chromatography eluting with a mixture of hexane and AcOEt (20:1-3:1) to give 1-tert-butyl 5-ethyl 2-[(acetyloxy)acetyl]pentanedioate as yellow oil (4.27 g).

後処理

  1. customThe mixture was partitioned between AcOEt and water
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. washeluting with a mixture of hexane and AcOEt (20:1-3:1)

出典と根拠

ORDレコード
ord-d6b9ba51eb2544649fd3b323771b8747
出典データセット
uspto-grants-2008_01
特許番号
US07317009B2

反応ノート

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