Diethyl Ether → HCID 86615013、化合物

HRID 732484ノート

反応式

HRID 732484 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 86615013HCID 86615013、化合物収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
32 °C

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-62320f7b3a914087bc12cfb79925fa21
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

反応ノート

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