Acetone → 4-Methylheptanoic acid, (-)-

HRID 130532

반응식

HRID 130532 반응식
[CH3:1][C:2](=[CH:4][CH2:5][CH2:6][C@H](C)CCC)[CH3:3].[OH2:12].C[C:14]([CH3:16])=[O:15]>OS(O)(=O)=O.[Cl-].[Na+].O>[CH3:1][C@H:2]([CH2:4][CH2:5][CH3:6])[CH2:3][CH2:16][C:14]([OH:12])=[O:15]

참가 물질

6

반응물 3

HCID 180AcetoneHCID 962Water2회HCID 15345839(6R)-2,6-Dimethylnon-2-ene

생성물 1

HCID 138003704-Methylheptanoic acid, (-)-

시약·촉매·용매 2

HCID 1118Sulfuric Acid용매2회HCID 57417360Sodium chloride; water용매

실험 절차

To alkene 98 (20 g, 0.13 mol) in acetone (433 mL) was added a solution of CrO3 (39 g, 0.39 mol) in H2SO4 (33 mL)/H2O (146 mL) over 50 minutes. After 6 hours a further amount of CrO3 (26 g, 0.26 mol) in H2SO4 (22 mL)/H2O (100 mL) was added. After 12 hours the solution was diluted with brine and the solution extracted with ether. The combined organic phases were dried (MgSO4) and concentrated. Flash chromatography (gradient of 6:1 to 2:1 hexane/EtOAc) gave the product 99 as an oil. 12.1 g; 65%. MS, m/z (relative intensity): 143 [M−H, 100%].

후처리

  1. extractionthe solution extracted with ether
  2. dry with materialThe combined organic phases were dried (MgSO4)
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-bf9b1fd46063406582f2686e97772940
출처 데이터셋
uspto-grants-2008_06
특허 번호
US07381747B2

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