Hydrochloric Acid → HCID 15839226, compound

HRID 743987Notes

Reaction equation

HRID 743987 reaction equation
C(NC(C)C)(C)C.[Li]CCCC.CCCCCC.[CH2:19]1[O:27][C:26]2[CH:25]=[CH:24][C:23]([CH2:28][CH2:29][C:30]([O:32][CH3:33])=[O:31])=[CH:22][C:21]=2[O:20]1.[C:34]([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)(=[O:41])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.Cl>C1COCC1>[C:42]1([C:34]([C:35]2[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=2)([OH:41])[CH:29]([CH2:28][C:23]2[CH:24]=[CH:25][C:26]3[O:27][CH2:19][O:20][C:21]=3[CH:22]=2)[C:30]([O:32][CH3:33])=[O:31])[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=1

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 3102BenzophenoneHCID 7912DiisopropylamineHCID 8058HexaneHCID 10081775methyl 3-(3,4-methylenedioxyphenyl)-propionateHCID 178418339Butyllithium

Product 1

HCID 15839226HCID 15839226, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a solution of di-isopropylamine (0.52 ml, 3.69 mmol) in dry THF (3 ml) at 0° C. under argon was added n-BuLi in hexane (1.36 ml, 2.5 M, 3.4 mmol). After stirring for 40 min the solution was cooled to -78° C. and a solution of methyl 3-(3,4-methylenedioxyphenyl)-propanoate (0.592 g, 2.84 mmol) in dry THF (2 ml) was added dropwise over 7 min. After a further 2 min a solution of benzophenone (0.517 g, 2.84 mmol) in dry THF (2 ml) was added dropwise. After a further 30 min at -78° C. the mixture was warmed to 0° C. over 30 min and poured into 1M aqueous HCl. The product was extracted with EtOAc (3X). The combined organic extract was washed with water (2X) then brine. After drying (Na2SO4 anhydrous), filtration and evaporation gave an off-white solid. Recrystallization from hot hexane gave the title compound (0.835 g, 76% yield) as a colorless solid.

Workup

  1. temperatureAfter a further 30 min at -78° C. the mixture was warmed to 0° C. over 30 min
  2. extractionThe product was extracted with EtOAc (3X)
  3. extractionThe combined organic extract
  4. washwas washed with water (2X)
  5. customAfter drying
  6. filtration(Na2SO4 anhydrous), filtration and evaporation
  7. customgave an off-white solid
  8. customRecrystallization from hot hexane

Sources & evidence

ORD record
ord-e165b3663b4044d0993691f0cffb21c8
Source dataset
uspto-grants-1996_09
Patent number
US05559105

Reaction notes

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