Triethylamine → (+/-)-Methyl 6,8-bis(methylsulfonyloxy)octanoate

HRID 370326노트

반응식

HRID 370326 반응식
C(N(CC)CC)C.[CH3:8][S:9](Cl)(=[O:11])=[O:10].[OH:13][CH:14]([CH2:23][CH2:24][OH:25])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20]>ClCCl>[CH3:8][S:9]([O:13][CH:14]([CH2:23][CH2:24][O:25][S:9]([CH3:8])(=[O:11])=[O:10])[CH2:15][CH2:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])(=[O:11])=[O:10]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 113559606,8-Dihydroxyoctanoic acid methyl ester

생성물 1

HCID 13888693(+/-)-Methyl 6,8-bis(methylsulfonyloxy)octanoate수율 99.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

Under an argon atmosphere, triethylamine (0.7 ml, 5.05 mmol) and methanesulfonyl chloride (0.3 ml, 3.71 mmol) were added to a solution of (±)-methyl 6,8-dihydroxyoctanoate (320 mg, 1.68 mmol) in dichloromethane (8.4 ml) at 0° C. The mixture was stirred at 0° C. for 30 min, then quenched with ice water (20 ml) and extracted with dichloromethane (20 ml). The organic extract was washed with 2 M hydrochloric acid (20 ml), saturated sodium bicarbonate solution (20 ml) and brine (20 ml). The organic phase was dried over magnesium sulphate and the solvent was evaporated under reduced pressure to give the crude product which was purified using flash column chromatography with hexane-ethyl acetate (2:3) to give (±)-methyl 6,8-bis(methylsulfonyloxy)octanoate (581 mg, 99% yield) as a clear yellow oil. Rf 0.30 (hexane-ethyl acetate, 3:2).

후처리

  1. customquenched with ice water (20 ml)
  2. extractionextracted with dichloromethane (20 ml)
  3. extractionThe organic extract
  4. washwas washed with 2 M hydrochloric acid (20 ml), saturated sodium bicarbonate solution (20 ml) and brine (20 ml)
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. customthe solvent was evaporated under reduced pressure
  7. customto give the crude product which
  8. customwas purified

출처 및 근거

ORD 기록
ord-1eda75f3caff47d18670265111cb749a
출처 데이터셋
uspto-grants-2000_10
특허 번호
US06140512

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