N-bromobutanimide → Ethyl acetate hexane

HRID 843210Notes

Reaction equation

HRID 843210 reaction equation
BrN1[C:6](=[O:7])[CH2:5][CH2:4][C:3]1=O.[CH2:9](N(S(F)(F)F)[CH2:12][CH3:13])[CH3:10].C(=O)(O)[O-:19].[Na+]>ClCCl>[C:12]([O:7][CH2:6][CH3:5])(=[O:19])[CH3:13].[CH3:3][CH2:4][CH2:5][CH2:6][CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 123472(Diethylamino)sulfur trifluorideHCID 516892Sodium Bicarbonate

Product 1

HCID 21226206Ethyl acetate hexaneYield 45%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (1,2 g) and diethylaminosulphur trifluoride (1,2 g) are added to a solution of the pivaloyl ester (49) (2 g) in dichloromethane (100 ml) at 0° C. After 1 hour, saturated sodium bicarbonate is added. The dichloromethane layer is dried (MgSO4), filtered and evaporated. The β-fluoropyranoside (50) is purified by silica gel column chromatography eluting with ethyl acetate:hexane (2:8), (yield 45%).

Workup

  1. dry with materialThe dichloromethane layer is dried (MgSO4)
  2. filtrationfiltered
  3. customevaporated
  4. customThe β-fluoropyranoside (50) is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-aefabc23581a4ad5a9f320e63d671d3e
Source dataset
uspto-grants-2002_04
Patent number
US06376657B1

Reaction notes

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