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

HRID 370326ノート

反応式

HRID 370326 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-1eda75f3caff47d18670265111cb749a
出典データセット
uspto-grants-2000_10
特許番号
US06140512

反応ノート

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