Trifluoromethanesulfonic acid → Ethyl (2S)-2-(benzyloxy)propanoate

HRID 278465Notes

Reaction equation

HRID 278465 reaction equation
FC(F)(F)S(O)(=O)=O.[C:9]([O:14][CH2:15][CH3:16])(=[O:13])[C@H:10]([CH3:12])[OH:11].ClC(Cl)(Cl)C(=N)O[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C1CCCCC1.C(Cl)Cl>[CH2:21]([O:11][C@@H:10]([CH3:12])[C:9]([O:14][CH2:15][CH3:16])=[O:13])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 62406Trifluoromethanesulfonic acidHCID 92831(L)-ethyl lactateHCID 144968Benzyl 2,2,2-trichloroacetimidate

Product 1

HCID 10058881Ethyl (2S)-2-(benzyloxy)propanoateYield 62.3%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8078CyclohexaneSolvent

Procedure

Trifluoromethanesulfonic acid (1.13 g) was added to a stirred mixture of ethyl (S)-(−)-lactate (5.90 g) and benzyl 2,2,2-trichloroacetimidate (15.15 g) in cyclohexane (70 ml) and methylene chloride (35 ml) at room temperature under nitrogen atmosphere. After being stirred for 18 hours, the reaction mixture was filtered. The filtrate was diluted with cyclohexane, and then washed successively with saturated NaHCO3 solution (100 ml)and H2O (100 ml). The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel (260 g) chromatography eluted with hexane/ethyl acetate (30:1) to give ethyl (S)-2-(benzyloxy)propionate (6.48 g).

Workup

  1. filtrationthe reaction mixture was filtered
  2. additionThe filtrate was diluted with cyclohexane
  3. washwashed successively with saturated NaHCO3 solution (100 ml)and H2O (100 ml)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel (260 g) chromatography
  7. washeluted with hexane/ethyl acetate (30:1)

Sources & evidence

ORD record
ord-f1eaf8f197e340eeb929eb53e43d9a47
Source dataset
uspto-grants-2002_03
Patent number
US06359145B1

Reaction notes

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