Pyridine → HCID 21468971, compound

HRID 866274Notes

Reaction equation

HRID 866274 reaction equation
[S:1]([O:8]S(C(F)(F)F)(=O)=O)([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2].N1C=CC=CC=1.[CH2:22]([C:29](O)([CH2:33][CH2:34][CH2:35][CH3:36])[C:30]([OH:32])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)Cl>[CH2:22]([C:29]([O:8][S:1]([C:4]([F:7])([F:6])[F:5])(=[O:3])=[O:2])([CH2:33][CH2:34][CH2:35][CH3:36])[C:30]([OH:32])=[O:31])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 19967213HCID 19967213, compound

Product 1

HCID 21468971HCID 21468971, compoundYield 67.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Triflic anhydride (71 mmoles, 20 g) was added at -27° C. to a solution of pyridine (74 moles, 5.9 g) in 150 ml methylene chloride with vigorous stirring. The solution was warmed to room temperature. Benzyl 2-hydroxyhexanoic acid (57 moles, 12.65 g) in 15 ml methylene chloride was added over 2 minutes. The solution was stirred for 1 hour and filtered. The filtrate was concentrated, filtered through silica gel eluted with hexane, and evaporated to yield 17.0 g of benzyl 2-(trifluoromethanesulfonylhydroxy)hexanoic acid. (MS)

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated
  3. filtrationfiltered through silica gel
  4. washeluted with hexane
  5. customevaporated

Sources & evidence

ORD record
ord-e6674a73b3b047d9b1c5ce5e88263aec
Source dataset
uspto-grants-1996_10
Patent number
US05569768

Reaction notes

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