Triethylamine → Methyl 1-((acetylthio)methyl)cyclopropaneacetate

HRID 22428

반응식

HRID 22428 반응식
OC[C:3]1([CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH2:5][CH2:4]1.CCN([CH2:16][CH3:17])CC.[CH3:18][S:19](Cl)(=O)=O.S([O-])(=O)(=[O:25])C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CN(C=O)C>[C:16]([S:19][CH2:18][C:3]1([CH2:6][C:7]([O:9][CH3:10])=[O:8])[CH2:4][CH2:5]1)(=[O:25])[CH3:17]

참가 물질

8

반응물 5

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 85257MethanesulfonateHCID 516892Sodium BicarbonateHCID 29941748(1-Hydroxymethylcyclopropyl)acetic acid methyl ester

생성물 1

HCID 53482060Methyl 1-((acetylthio)methyl)cyclopropaneacetate

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
-10 °C

실험 절차

To a solution of the alcohol of Step 4 (28.2 g, 0.20 mol) and Et3N (82 mL, 0.59 mol) in CH2Cl2 (1 L) cooled to -40° C. was added methanesulfonyl chloride (43.5 mL, 0.3 mol). The reaction mixture was warmed to -10° C. for 20 min and then an aqueous solution of NaHC03 was added. The product was extracted with CH2Cl2, washed with brine and dried over Na2SO4. A portion of this mesylate (0.053 mol) was then dissolved in DMF (180 mL) and cooled to 0° C. Freshly prepared cesium thiol acetate (J. Org. Chem., 51, 3664, (1986)) (22 g, 0.11 mol) was added and the mixture was stirred overnight at r.t. The reaction mixture was poured into an aqueous solution of NaHCO3 and extracted with Et2O. The organic phases were washed with brine and dried over Na2SO4. The residual oil was then purified by flash chromatography with 10:1 hexane:EtOAc to yield 7.5 g, 70%, of the title compound. 1H NMR (CDCl3) δ0.60 (4H, m), 2.30 (2H, s), 2.35 (3H, s), 3.03 (2H, s), 3.70 (3H, s).

후처리

  1. additionan aqueous solution of NaHC03 was added
  2. extractionThe product was extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. temperaturecooled to 0° C
  6. extractionextracted with Et2O
  7. washThe organic phases were washed with brine
  8. dry with materialdried over Na2SO4
  9. customThe residual oil was then purified by flash chromatography with 10:1 hexane
  10. customEtOAc to yield 7.5 g, 70%

출처 및 근거

ORD 기록
ord-52d2284b10684dea8050d38f183854a8
출처 데이터셋
uspto-grants-1995_06
특허 번호
US05428033

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