2,6-Lutidine → HCID 86705576, compound

HRID 2279593Notes

Reaction equation

HRID 2279593 reaction equation
[OH:1][C@@H:2]([CH2:8][CH2:9][I:10])[C:3]([O:5][CH2:6][CH3:7])=[O:4].N1C(C)=CC=CC=1C.FC(F)(F)S(O[Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])(=O)=O>C(Cl)Cl>[I:10][CH2:9][CH2:8][C@H:2]([O:1][Si:25]([CH2:30][CH3:31])([CH2:28][CH3:29])[CH2:26][CH3:27])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 2733308Triethylsilyl trifluoromethanesulphonateHCID 11747272HCID 11747272, compound

Product 1

HCID 86705576HCID 86705576, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 392 (15.5 g, 60.1 mmol), 2,6-lutidine (21.0 ml, 180 mmol) and DCM (125 mL) cooled to 0° C. and maintained under N2 was added dropwise triethylsilyl trifluoromethanesulfonate (17.5 g, 66.1 mmol). The reaction was stirred at 0° C. for 1 h then warmed to RT and stirred for 18 h. The reaction was quenched by adding satd. aq. NH4Cl and extracted with DCM. The organic extract was washed organic with brine, dried (Na2SO4), filtered and concentrated. The crude product was purified by SiO2 chromatography (SNAP 100) eluting with EtOAc/hexane (9:1) to afford 18.9 g (76%) of (S)-ethyl 4-iodo-2-(triethylsilyloxy)butanoate (396) as a yellow oil.

Workup

  1. temperaturemaintained under N2
  2. temperaturethen warmed to RT
  3. stirringstirred for 18 h
  4. customThe reaction was quenched
  5. additionby adding satd
  6. extractionaq. NH4Cl and extracted with DCM
  7. extractionThe organic extract
  8. washwas washed organic with brine
  9. dry with materialdried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was purified by SiO2 chromatography (SNAP 100)
  13. washeluting with EtOAc/hexane (9:1)

Sources & evidence

ORD record
ord-158a9e7b711d4d988e4440d39776f2ff
Source dataset
uspto-grants-2015_09
Patent number
US09133187B2

Reaction notes

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