Diethyl Ether → HCID 86615013, 화합물

HRID 732484노트

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HRID 732484 반응식
[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH2:18][OH:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.C(OCC)C.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:1]([O:3][C:4](=[O:20])[C:5]1[CH:17]=[C:16]([CH:18]=[O:19])[CH:15]=[C:7]([C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])=[O:9])[CH:6]=1)[CH3:2]

참가 물질

6

반응물 4

HCID 3283Diethyl EtherHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 688164795-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester

생성물 1

HCID 86615013HCID 86615013, 화합물수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
32 °C

실험 절차

Add a solution of 5-hydroxymethyl-N-methyl-N-propyl-isophthalamic acid ethyl ester (600 mg, 2.15 mmol) dropwise to a mixture of Dess-Martin periodinane (1.06 g, 2.5 mmol) in dichloromethane (6.5 mL). Stir the exothermic reaction mixture (32° C.) for 20 min without additional heat. To the reaction mixture add diethyl ether (12 mL) and saturated aqueous sodium bicarbonate (12 mL). Separate the layers and wash the aqueous layer with diethyl ether (2×12 mL). Combine the organics and wash with saturated aqueous sodium bicarbonate (12 mL), saturated aqueous sodium chloride (12 mL), dry (magnesium sulfate), concentrate, and purify (silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes) to give the title compound as an oil (0.54 g, 91%).

후처리

  1. customSeparate the layers
  2. washwash the aqueous layer with diethyl ether (2×12 mL)
  3. washCombine the organics and wash with saturated aqueous sodium bicarbonate (12 mL), saturated aqueous sodium chloride (12 mL)
  4. dry with materialdry (magnesium sulfate)
  5. concentrationconcentrate
  6. custompurify
  7. wash(silica gel chromatography, eluting with 50:50 ethyl acetate:hexanes)

출처 및 근거

ORD 기록
ord-62320f7b3a914087bc12cfb79925fa21
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07585885B2

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