2,6-Lutidine → HCID 86606508, compound

HRID 1987827Notes

Reaction equation

HRID 1987827 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].O[CH2:17][C@H:18]1[O:22][C:21](=[O:23])[CH2:20][CH2:19]1.N1C(C)=CC=CC=1C>C(Cl)Cl>[F:1][C:2]([F:15])([F:14])[S:3]([O:6][CH2:17][C@@H:18]1[CH2:19][CH2:20][C:21](=[O:23])[O:22]1)(=[O:5])=[O:4]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 67749Trifluoromethanesulfonic anhydrideHCID 2733813(S)-(+)-gamma-Hydroxymethyl-gamma-butyrolactone

Product 1

HCID 86606508HCID 86606508, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Trifluoromethanesulfonic anhydride (0.97 g, 3.4 mmol) was added dropwise to a 0° C. solution of (S)-5-(hydroxymethyl)-dihydrofuran-2(3H)-one (0.20 g, 1.7 mmol) and lutidine (0.41 g, 3.8 mmol) in CH2Cl2 (2 mL). The reaction was stirred at 0° C. for 1.5 hours, then diluted with 1:4 EtOAc/hexanes and passed through a plug of silica gel. The volatiles were removed under reduced pressure to yield a yellow oil which was used immediately without purification (0.38 g, 89%).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. customto yield a yellow oil which
  3. customwas used immediately without purification (0.38 g, 89%)

Sources & evidence

ORD record
ord-f37a7a5be89e44859de7fde799f12121
Source dataset
uspto-grants-2009_06
Patent number
US07553842B2

Reaction notes

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