Dimethylformamide → 3-(3,5-Dichloro-4-formylphenyl)-propionic acid tert-butyl ester

HRID 1360794

反応式

HRID 1360794 の反応式
[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[CH:12]=[C:11]([Cl:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])(CC)C.CN([CH:26]=[O:27])C>C1COCC1>[C:1]([O:5][C:6](=[O:17])[CH2:7][CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([CH:26]=[O:27])=[C:11]([Cl:16])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 669653423-(3,5-Dichlorophenyl)-propionic acid tert-butyl esterHCID 178418400CID 53628100

生成物 1

HCID 866328253-(3,5-Dichloro-4-formylphenyl)-propionic acid tert-butyl ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 3-(3,5-Dichloro-phenyl)-propionic acid tert butyl ester (1 g, 3.6 mmol) in THF (50 mL) at −78 C was added dropwise s-butyl lithium (1.4 M cyclohexanes; 5.7 mL, 2.2 eq). The resulting red colored homogeneous solution was stirred under nitrogen at −78 C for one hour, at which time DMF (560 mL, 2 eq) was added. After 30 minutes, quenched reaction with saturated ammonium chloride solution at −78 C. Removed ice bath and allowed reaction to reach room temperature. Evaporation of volatiles in vacuo, partitioned between water and ethyl acetate. Combined ethyl acetate fractions were dried over magnesium sulfate and appropriately loaded onto a silica gel column. Isolated 600 mg of titled compound after chromatography (isocratic 20% ethyl acetate/n-heptanes). 1H NMR (400 MHz, CHLOROFORM-D) δ ppm 1.35-1.44 (m, 10H) 2.55 (t, J=7.45 Hz, 2H) 2.90 (t, J=7.45 Hz, 2H) 7.23 (s, 2H) 10.45 (s, 1H).

後処理

  1. additionwas added
  2. customquenched
  3. customreaction with saturated ammonium chloride solution at −78 C
  4. customRemoved ice bath and allowed
  5. customreaction
  6. customto reach room temperature
  7. customEvaporation of volatiles in vacuo
  8. custompartitioned between water and ethyl acetate
  9. dry with materialCombined ethyl acetate fractions were dried over magnesium sulfate

出典と根拠

ORDレコード
ord-ffce2ba158674c2c9a561fcc2f77ced6
出典データセット
uspto-grants-2011_02
特許番号
US07879850B2

関連ノート

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