Iodoethane → 2-Ethyl-3-methyl-3-phenylbutanoic acid

HRID 133844

反応式

HRID 133844 の反応式
[CH3:1][C:2]([CH3:13])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH2:3][C:4]([OH:6])=[O:5].C(=O)=O.[CH3:17][C:18](C)=O.C([N-]C(C)C)(C)C.[Li+].CN1CCCN(C)C1=O.C(I)C>O1CCCC1>[CH2:17]([CH:3]([C:2]([CH3:13])([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:1])[C:4]([OH:6])=[O:5])[CH3:18]

参加物

7

反応物 5

HCID 6340IodoethaneHCID 13890beta-Phenylisovaleric acidHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 2724682Lithium diisopropylamideHCID 18522661Acetone cardice

生成物 1

HCID 112757642-Ethyl-3-methyl-3-phenylbutanoic acid収率 30%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

In accordance with a modified literature procedure (Pfeffer, P. E.; Silbert, L. S.; Chirinko, J. M. J. Org. Chem. 37(3), 1972, 451-458), a solution of 3,3-dimethyl-3-phenyl propionic acid (0.47 g, 2.6 mmol, from Reference Example 22) in tetrahydrofuran (4.5 mL) is cooled to −40° C. (dry ice/acetone) while stirring under a nitrogen atmosphere. Lithium diisopropylamide (Aldrich, 2.0 M solution in tetrahydrofuran/ethylbenzene/heptane, 2.9 mL, 5.8 mmol) is added dropwise via syringe, followed by 1,3-dimethyl-3,4,5,6-tetrahydro-2(1 H)-pyrimidinone (DMPU, 0.35 mL, 2.9 mmol). The reaction mixture is then allowed to warm to room temperature and to stir for 30 minutes before being re-cooled to 0° C. (ice water bath). Ethyl iodide (0.31 mL, 3.9 mmol) is then added neat via syringe and the reaction mixture is allowed to stir overnight while warming to room temperature. The reaction is quenched by the addition of 10% aqueous hydrochloric acid solution and extracted thrice with ethyl acetate. The combined extracts are washed twice with 10% aqueous hydrochloric acid solution and once with saturated sodium chloride solution, dried over anhydrous sodium sulfite, and concentrated under reduced pressure. The crude solid is recrystallized from hexanes to afford pure material as a white solid (0.16 g, 30%). MS (ES−): (M−H)=205.0

後処理

  1. stirringto stir for 30 minutes
  2. stirringto stir overnight
  3. temperaturewhile warming to room temperature
  4. customThe reaction is quenched by the addition of 10% aqueous hydrochloric acid solution
  5. extractionextracted thrice with ethyl acetate
  6. washThe combined extracts are washed twice with 10% aqueous hydrochloric acid solution and once with saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfite
  8. concentrationconcentrated under reduced pressure
  9. customThe crude solid is recrystallized from hexanes

出典と根拠

ORDレコード
ord-169b938c99dd42ff95790050937bc2a3
出典データセット
uspto-grants-2008_06
特許番号
US07390910B2

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