Pyridine → HCID 23284299, compound

HRID 368959Notes

Reaction equation

HRID 368959 reaction equation
[F:1][C:2]([F:8])([F:7])[S:3]([OH:6])(=[O:5])=[O:4].N1C=CC=CC=1.[CH2:15]([O:18][CH2:19][C@H:20]([O:23][CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:21]O)[CH:16]=[CH2:17]>ClCCl>[CH2:15]([O:18][CH2:19][CH:20]([O:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:21][O:4][S:3]([C:2]([F:8])([F:7])[F:1])(=[O:6])=[O:5])[CH:16]=[CH2:17]

Participants

5

Reactant 3

HCID 1049PyridineHCID 62406Trifluoromethanesulfonic acidHCID 70198362-O-Benzyl-3-O-allyl-sn-glycerol

Product 1

HCID 23284299HCID 23284299, compoundYield 101.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Trifluoromethanesulfonic acid (5.95 ml, 36.3 mmol) is added dropwise at -30° C. to a mixture of dichloromethane (130 ml) and pyridine (3.19 g, 40.3 mmol). Compound 12 (8.95 g, 40.3 mmol) in dichloromethane (60 ml) is then added dropwise at -25° C. The mixture is allowed to come to room temperature and is concentrated in vacuo, and the residue is chromatographed (hexane/ethyl acetate 6:1). Compound 13a (13 g, 91%) is obtained.

Workup

  1. customto come to room temperature
  2. concentrationis concentrated in vacuo
  3. customthe residue is chromatographed (hexane/ethyl acetate 6:1)

Sources & evidence

ORD record
ord-fa22e951ba8a48818c3ee012bbdb24e5
Source dataset
uspto-grants-2000_10
Patent number
US06136790

Reaction notes

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