Acetic Acid → HCID 22935663, compound

HRID 853745Notes

Reaction equation

HRID 853745 reaction equation
[Li+].[CH3:2]CC[CH2-].C(NC(C)C)(C)C.CN1C(=O)N(C)CCC1.[CH3:22][C:23]1[CH2:24][C:25]2([CH2:31][CH:32]([CH3:34])[CH:33]=1)[C:29](=[O:30])[CH2:28][CH2:27][CH2:26]2.CI.C(O)(=O)C>C1COCC1>[CH3:2][CH:28]1[CH2:27][CH2:26][C:25]2([CH2:31][CH:32]([CH3:34])[CH:33]=[C:23]([CH3:22])[CH2:24]2)[C:29]1=[O:30]

Participants

8

Reactant 6

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 61028n-Butyl lithiumHCID 816462(1H)-Pyrimidinone, tetrahydro-1,3-dimethyl-HCID 12093582HCID 12093582, compound

Product 1

HCID 22935663HCID 22935663, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-40 °C

Procedure

N-Butyllithium (1.6 M in hexanes, 172 ml, 0.275 mol) was added to a solution of diisopropylamine (30.4 g, 0.3 mol) in THF (300 ml), while maintaining the internal temperature around −40° C. Then DMPU (1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone) (38.4 g, 0.3 mol) was added, followed, after 15 minutes, by a mixture of 6,8 and 7,9-dimethylspiro[4,5]dec-7-en-1-one (44.74 g, 0.25 mol) in THF (50 ml) in 30 minutes. After stirring for 30 more minutes, methyl iodide (106 g, 0.75 mol) was added rapidly. After 15 minutes, the reaction was quickly warmed up to 0° C. Acetic acid (18.6 g, 0.31 mol) was added and the reaction warmed up to room temperature. The reaction was quenched with water (500 ml) and extracted twice with pentane. Each organic fraction was treated successively with water, aqueous NaHSO3, aqueous saturated NaHCO3, and brine. Combined organic fractions were dried over Na2SO4. The liquid obtained after filtration and evaporation of solvents was purified by bulb to bulb distillation (B.p.=105° C./0.47 mbar). The title product was obtained as a colorless liquid (42.85 g, yield=89%), as a mixture of isomers.

Workup

  1. additionwas added rapidly
  2. temperaturethe reaction was quickly warmed up to 0° C
  3. temperaturethe reaction warmed up to room temperature
  4. customThe reaction was quenched with water (500 ml)
  5. extractionextracted twice with pentane
  6. additionEach organic fraction was treated successively with water, aqueous NaHSO3, aqueous saturated NaHCO3, and brine
  7. dry with materialCombined organic fractions were dried over Na2SO4
  8. customThe liquid obtained
  9. filtrationafter filtration and evaporation of solvents
  10. distillationwas purified by bulb to bulb distillation (B.p.=105° C./0.47 mbar)

Sources & evidence

ORD record
ord-867958f6139f4d56af9475879199e375
Source dataset
uspto-grants-2007_08
Patent number
US07256170B2

Reaction notes

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