Iodoethane → HCID 18172351, compound

HRID 2101798Notes

Reaction equation

HRID 2101798 reaction equation
[CH:1]([N-]C(C)C)(C)[CH3:2].[Li+].[C:9]1([CH2:15][O:16][C:17]2[CH:22]=[CH:21][C:20]([CH2:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])=[CH:19][CH:18]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.ICC>C1COCC1.CN1CCCN(C)C1=O>[C:9]1([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH:24]([CH2:1][CH3:2])[C:25]([O:27][CH3:28])=[O:26])=[CH:21][CH:22]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 525519Methyl 3-[4-(benzyloxy)phenyl]propanoateHCID 2724682Lithium diisopropylamide

Product 1

HCID 18172351HCID 18172351, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-Solvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of lithium diisopropylamide (6.5 mL, 2.0 M in heptane/THF/ethylbenzene) in THF (25.0 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (5.0 mL) was added methyl 3-(4-(benzyloxy)phenyl)propanoate 23.1 (3.00 g, 11 mmol) in THF (10 mL) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (2.5 mL) at −78° C. The resulting mixture was stirred at −78° C. for 30 minutes and then iodoethane (1.0 mL, 13 mmol) in THF (5.0 mL) was added. The reaction mixture was stirred at the same temperature for 20 minutes. The reaction was then stirred at room temperature for 16 hours. The reaction was quenched with water (30.0 mL), and the mixture was concentrated in vacuo. The residue was dissolved in EtOAc (100 mL), washed with brine (2×25 mL), and dried with Na2SO4. The residue was purified by silica gel column (eluent with hexane/EtOAc; 85/15) to give the title compound 32.1. MS ESI (pos.) m/e: 299.0 (M+H)+.

Workup

  1. stirringThe reaction mixture was stirred at the same temperature for 20 minutes
  2. stirringThe reaction was then stirred at room temperature for 16 hours
  3. customThe reaction was quenched with water (30.0 mL)
  4. concentrationthe mixture was concentrated in vacuo
  5. dissolutionThe residue was dissolved in EtOAc (100 mL)
  6. washwashed with brine (2×25 mL)
  7. dry with materialdried with Na2SO4
  8. customThe residue was purified by silica gel column (eluent with hexane/EtOAc; 85/15)

Sources & evidence

ORD record
ord-a44f123b561347989ff7bd9ef9738925
Source dataset
uspto-grants-2009_08
Patent number
US07572934B2

Reaction notes

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