Methanesulfonyl chloride → HCID 247764, 화합물

HRID 2231625노트

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HRID 2231625 반응식
[CH3:1][C:2]1([CH3:11])[O:6][C@H:5]([CH2:7][OH:8])[C@@H:4]([CH2:9][OH:10])[O:3]1.[CH3:12][S:13](Cl)(=[O:15])=[O:14].C(=O)(O)[O-].[Na+]>N1C=CC=CC=1>[CH3:1][C:2]1([CH3:11])[O:3][C@H:4]([CH2:9][O:10][S:13]([CH3:12])(=[O:15])=[O:14])[C@@H:5]([CH2:7][O:8][S:13]([CH3:12])(=[O:15])=[O:14])[O:6]1

참가 물질

5

반응물 3

HCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 785244(-)-2,3-O-Isopropylidene-D-threitol

생성물 1

HCID 247764HCID 247764, 화합물수율 66%

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

The starting material (1) (3,4-O-isopropylidene-D-mannitol) was reacted with sodium periodate and potassium borohydride as described in J. Chem. Soc., Perkin Trans. I., 1972, 275 (the contents of which are herein incorporated by reference) to yield compound (2) in 92% yield. Compound (2) (5.1 g) was dissolved in pyridine (40 ml) and cooled in ice. To this solution was added methanesulphonyl chloride (18 ml), dropwise with stirring. The mixture was allowed to stand at room temperature for 3 hours, after which time it was added to a solution of sodium bicarbonate. This solution was then extracted with dichloromethane (5×50 ml) and the combined extracts were dried (MgSO4) and concentrated in vacuo. The residue obtained was recrystallised from ethanol to give 2,3-O-isopropylidene-1,4-di-O-methanesulphonyl-D-threitol (3), (6.6 g, 66%), m.p. 83°-85° C.

후처리

  1. temperaturecooled in ice
  2. extractionThis solution was then extracted with dichloromethane (5×50 ml)
  3. dry with materialthe combined extracts were dried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue obtained
  6. customwas recrystallised from ethanol

출처 및 근거

ORD 기록
ord-00b19121bf104c5b9bddcf2665e67340
출처 데이터셋
uspto-grants-1988_11
특허 번호
US04783452

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