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Ethyl 2-hydroxyisobutyrate → Ethyl 2-methyl-2-{[(4-nitrophenoxy)carbonyl]oxy}propanoate

HRID 2047474
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HRID 2047474 반응식
[OH:1][C:2]([CH3:9])([CH3:8])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:10](Cl)(=[O:21])[O:11][C:12]1[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=1>C(#N)C.CN(C1C=CN=CC=1)C.O>[CH3:8][C:2]([O:1][C:10]([O:11][C:12]1[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=1)=[O:21])([CH3:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 6653Ethyl 2-hydroxyisobutyrateHCID 821294-Nitrophenyl chloroformate

생성물 1

HCID 67232782Ethyl 2-methyl-2-{[(4-nitrophenoxy)carbonyl]oxy}propanoate수율 74%

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 962Water용매HCID 6342
Acetonitrile
용매

실험 절차

To a solution of ethyl 2-hydroxy-2-methylpropanoate (1.2 g) and 4-nitrophenyl chlorocarbonate (1.2 g) in acetonitrile (20 mL) was added DMAP (0.77 g) at 0° C., and the mixture was stirred at room temperature for 3 days. The mixture was diluted with water, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried and concentrated under reduced pressure. The residue was separated and purified by silica gel column chromatography (solvent gradient; 0→25% ethyl acetate/hexane) to give ethyl 2-methyl-2-{[(4-nitrophenoxy)carbonyl]oxy}propanoate (1.3 g, 74%) as a pale-yellow oil.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. customdried
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified by silica gel column chromatography (solvent gradient; 0→25% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-ffc2398177eb47e5a9845913ce9b6bb4
출처 데이터셋
uspto-grants-2013_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08592454B2

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