Dimethyl Sulfoxide → Benzyl 2,2-dimethyl-5-oxopentanoate

HRID 1367137노트

반응식

HRID 1367137 반응식
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH2:12][CH2:13][CH2:14][C:15]([CH3:27])([CH3:26])[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17].C(N(CC)CC)C>C(Cl)Cl>[CH3:26][C:15]([CH3:27])([CH2:14][CH2:13][CH:12]=[O:11])[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 66972971Benzyl 5-hydroxy-2,2-dimethylpentanoate

생성물 1

HCID 86616388Benzyl 2,2-dimethyl-5-oxopentanoate수율 91.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

To a −78° C. solution of oxalyl chloride (4.80 g, 37.8 mmol) in DCM (200 mL) was add DMSO (5.91 g, 75.6 mmol) dropwise over 10 minutes. After 25 minutes of additional stirring, a −78° C. solution of benzyl 5-hydroxy-2,2-dimethylpentanoate (4.06 g, 17.2 mmol, Step B) in DCM (200 mL) was added via cannula over 75 minutes. After stirring for an additional 30 minutes, triethylamine (13.9 g, 137 mmol) was added slowly over 25 minutes. The cooling bath was allowed to warm, while the reaction stirred for an additional 18 hours. Reaction solvent was then removed in vacuo, and the residue was dissolved in a mixture of diethyl ether and water (containing enough HCl to remain acidic). The organics were then dried over sodium sulfated, filtered and concentrated in vacuo to give the title compound (3.67 g), which was used without further purification.

후처리

  1. temperatureto warm, while the reaction
  2. stirringstirred for an additional 18 hours
  3. customReaction solvent
  4. customwas then removed in vacuo
  5. dissolutionthe residue was dissolved in a mixture of diethyl ether and water (containing enough HCl to remain acidic)
  6. dry with materialThe organics were then dried over sodium
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-77ba46740c1540038c993d7d54a35f7d
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07893079B2

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