Ethyl 2-methylacetoacetate → 5-Ethyloxycarbonyl-5-methyl-6-oxo-1-heptanesulfonic acid

HRID 1435164

반응식

HRID 1435164 반응식
[CH3:1][CH:2]([C:8]([CH3:10])=[O:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[H-].[Na+].[CH2:13]1[CH2:20][O:19][S:16](=[O:18])(=[O:17])[CH2:15][CH2:14]1>CN(C)C=O>[CH2:6]([O:5][C:3]([C:2]([CH3:1])([C:8](=[O:9])[CH3:10])[CH2:20][CH2:13][CH2:14][CH2:15][S:16]([OH:19])(=[O:18])=[O:17])=[O:4])[CH3:7]

참가 물질

5

반응물 3

HCID 701Ethyl 2-methylacetoacetateHCID 154111,4-Butane sultoneHCID 24758Sodium hydride

생성물 1

HCID 580840065-Ethyloxycarbonyl-5-methyl-6-oxo-1-heptanesulfonic acid수율 122.6%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매3회

실험 절차

Ethyl 2-methylacetoacetate (43.2 g) in N,N-dimethylformamide (25 ml) was added to a suspension of sodium hydride (12.0 g of 60% NaH in mineral oil) in N,N-dimethylformamide (100 ml), dropwise with ice-bath cooling. This mixture was allowed to warm to ambient temperature for 30 mins before re-cooling. 1,4-butanesultone (40.8 g) in N,N-dimethylformamide (25 ml) was then added dropwise. The final mixture was heated at 50° C. for 18 hrs, then quenched with 50 ml of water. The solvent was evaporated under vacuum; the residue was partitioned between water and diethyl ether. The aqueous layer was collected, washed with fresh diethyl ether and evaporated under vacuum; final drying was under high vacuum over phosphorus pentoxide. A yield of 103 g of 5-(ethoxycarbonyl)-5-methyl-6-oxoheptane-1-sulfonic acid was obtained.

후처리

  1. temperaturecooling
  2. temperaturebefore re-cooling
  3. customquenched with 50 ml of water
  4. customThe solvent was evaporated under vacuum
  5. customthe residue was partitioned between water and diethyl ether
  6. customThe aqueous layer was collected
  7. washwashed with fresh diethyl ether
  8. customevaporated under vacuum
  9. customfinal drying

출처 및 근거

ORD 기록
ord-7663d7c9aae042e28aae309888a66498
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07615646B2

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