Dimethyl Carbonate → HCID 58399499, compound

HRID 1807627Notes

Reaction equation

HRID 1807627 reaction equation
[Li+].C[CH:3]([N-:5][CH:6]([CH3:8])[CH3:7])[CH3:4].[C:9](=O)([O:12][CH3:13])[O:10]C.[CH3:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].C1C[O:25]CC1.C(C1C=CC=CC=1)C>C1COCC1>[CH2:15]([N:5]1[CH:6]([CH3:7])[CH2:8][CH:4]([C:9]([O:12][CH3:13])=[O:10])[C:3]1=[O:25])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 12021Dimethyl CarbonateHCID 2724682Lithium diisopropylamideHCID 22742125Tetrahydrofuran heptane ethylbenzol

Product 1

HCID 58399499HCID 58399499, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

A solution of A-1 (7.2 g, 38.0 mmol) at −78° C. in THF (100 ml) was treated with 38.0 ml (76 mmol) of a 2.0 M solution of LDA in heptane/THF/ethylbenzene. After stirring for 30 minutes at −78° C., 6.85 g (76 mmol) of dimethyl carbonate was added and the solution was warmed to room temperature and allowed to stir for 6 hours. The reaction was quenched with 1M aqueous HCl and extracted three times with EtOAc. The combined organic extracts were washed with water, brine, dried over MgSO4, filtered and concentrated by rotary evaporation. The residue was purified on silica gel with EtOAc in hexanes to provide a mixture of diastereomers A-2 as an amber oil. The mixture was carried through the following sequence without separation. Data for A-2: LC/MS rt=1.62 min; m/z (M+H)=248.0 found: 248.1 required.

Workup

  1. temperaturethe solution was warmed to room temperature
  2. stirringto stir for 6 hours
  3. customThe reaction was quenched with 1M aqueous HCl
  4. extractionextracted three times with EtOAc
  5. washThe combined organic extracts were washed with water, brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified on silica gel with EtOAc in hexanes
  10. customto provide
  11. additiona mixture of diastereomers A-2 as an amber oil
  12. customThe mixture was carried through the following sequence without separation
  13. customLC/MS rt=1.62 min

Sources & evidence

ORD record
ord-34c020581f1044ddbc665297db0c5c5f
Source dataset
uspto-grants-2013_01
Patent number
US08357709B2

Reaction notes

Loading…