Lithium Hydroxide → HCID 72214380, compound

HRID 1777761Notes

Reaction equation

HRID 1777761 reaction equation
C([N-]C(C)C)(C)C.[Li+].[N:9]1[C:14]([CH3:15])=[CH:13][C:12]([CH3:16])=[CH:11][C:10]=1[CH3:17].C([O:20][C:21](=O)[O:22]CC)C.[Li+].[OH-]>C1COCC1>[CH3:17][C:10]1[CH:11]=[C:12]([CH2:16][C:21]([OH:22])=[O:20])[CH:13]=[C:14]([CH3:15])[N:9]=1

Participants

6

Reactant 4

HCID 3939Lithium HydroxideHCID 7766Diethyl CarbonateHCID 79532,4,6-TrimethylpyridineHCID 2724682Lithium diisopropylamide

Product 1

HCID 72214380HCID 72214380, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of lithium diisopropylamide (2M in THF/Hept/ethylbenzene, 5 mL) was added a solution of 2,4,6-collidine (1.26 mL) in THF (5 mL). The reaction mixture was stirred at RT for 4 h and added dropwise to a solution of diethylcarbonate (1.38 mL) in THF (5 mL) over 15 min. The resulting mixture was stirred at RT for 20 h. A LiOH solution (1M in water, 28 mL) was added, the mixture was stirred at RT for 2 h and filtered off. The filtrate was evaporated in vacuo. The residue was purified by preparative LC-MS (X) to afford 30 mg of yellow oil as mixture of two regioisomers. LC-MS (E): tR=0.17 min; [M+H]+: 165.97.

Workup

  1. stirringThe resulting mixture was stirred at RT for 20 h
  2. stirringthe mixture was stirred at RT for 2 h
  3. filtrationfiltered off
  4. customThe filtrate was evaporated in vacuo
  5. customThe residue was purified by preparative LC-MS (X)

Sources & evidence

ORD record
ord-37530d7146284713bff1e716fc4f3aa4
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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