Hydrochloric Acid → HCID 86740123, compound

HRID 463055Notes

Reaction equation

HRID 463055 reaction equation
[CH:1](NC(C)C)([CH3:3])[CH3:2].[C:8]1([C:14]([C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:15][CH2:16][CH2:17][CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.Cl.C(=O)([O-])[OH:32].[Na+]>O1CCCC1.CC(C)=O>[OH:32][C:1]([CH:19]([CH2:18][CH2:17][CH2:16]/[CH:15]=[C:14](\[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)/[C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C:20]([O:22][CH3:23])=[O:21])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 516892Sodium BicarbonateHCID 53901036HCID 53901036, compound

Product 1

HCID 86740123HCID 86740123, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

Diisopropylamine (0.8 g, 8 mmole) was dissolved in tetrahydrofuran (10 ml) under argon, and the solution was cooled at -70° C., followed by adding dropwise 1.6M n-butyl lithium-hexane solution (5 ml) and stirring for 5 minutes. A tetrahydrofuran (2 ml) solution containing methyl 7-phenyl-7-(3-pyridyl)-6-heptenoate (1.19 g, 4 mmole) was added dropwise to the reaction solution. After stirring for 15 minutes under the same reaction conditions, acetone (0.5 ml) was added, and the reaction was carried out for another 10 minutes. Subsequently, 2N hydrochloric acid (5 ml) was added to terminate the reaction, and the temperature of the solution was allowed to rise to room temperature, followed by adding aqueous sodium hydrogencarbonate to adjust to pH 8. The product was extracted with ethyl acetate, and the organic layer was washed with water and dried. The residue was chromatographed on silica gel using isopropyl ether:ethyl acetate (1:1) to yield methyl (E)-2-(1-hydroxy-1-methylethyl)- 7-phenyl-7-(3-pyridyl)-6-heptenoate (5-a) (1.2 g).

Workup

  1. additionby adding dropwise 1.6M n-butyl lithium-hexane solution (5 ml)
  2. additionwas added dropwise to the reaction solution
  3. additionwas added
  4. waitthe reaction was carried out for another 10 minutes
  5. customto terminate
  6. customthe reaction
  7. customto rise to room temperature
  8. extractionThe product was extracted with ethyl acetate
  9. washthe organic layer was washed with water
  10. customdried
  11. customThe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-17882cbbfd964021b5b84bfa8d5c5fcd
Source dataset
uspto-grants-1985_05
Patent number
US04518602

Reaction notes

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