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

HRID 860491노트

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HRID 860491 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-cb3ed2a8d94a473e92376235badcd6ad
출처 데이터셋
uspto-grants-2006_12
특허 번호
US07153854B2

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