Methanesulfonyl chloride → HCID 247764、化合物

HRID 2231625ノート

反応式

HRID 2231625 の反応式
[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

参加物

5

反応物 3

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

生成物 1

HCID 247764HCID 247764、化合物収率 66%

試薬・触媒・溶媒 1

HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-00b19121bf104c5b9bddcf2665e67340
出典データセット
uspto-grants-1988_11
特許番号
US04783452

反応ノート

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