Hydrochloric Acid → HCID 14373430, compound

HRID 1763165Notes

Reaction equation

HRID 1763165 reaction equation
[Mg].[OH:2][C:3]([CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][C:5]([O:7][CH3:8])=[O:6].C1COCC1.[C:19](Cl)(=[O:23])[CH:20]([CH3:22])[CH3:21].Cl>C1(C)C=CC=CC=1>[C:19]([CH:9]([C:3](=[O:2])[CH2:4][C:5]([O:7][CH3:8])=[O:6])[C:10]([O:12][CH3:13])=[O:11])(=[O:23])[CH:20]([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 62325Isobutyryl chlorideHCID 86741825HCID 86741825, compound

Product 1

HCID 14373430HCID 14373430, compoundYield 167.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 12.15 g (0.03 mol) of product of Step A in 50 ml of toluene was refluxed using a Dean-Stark trap for 1 hour. The resulting clear solution was cooled to room temperature and 50 ml of anhydrous THF were added. To this solution 6.4 g (6.3 ml, 0.06 mol) of isobutyryl chloride was added and stirred for 18 hours. Crude was poured into 3.7% HCl, extracted with EtOAc, the EtOAc layer was washed again with 3.7% HCl and saturated NaCl. Organic layer was dried (MgSO4) and removed in vacuo affording 12.3 g of crude dimethyl 2-(isobutyryl)-3-oxo-1,5-pentanedioate. The crude was purified by HPLC using 10% EtOAc/cyclohexane as eluting solvent affording 8.87 g (61%) of this intermediate as a light yellow oil; nD25 1.4783.

Workup

  1. temperaturewas refluxed
  2. customfor 1 hour
  3. extractionextracted with EtOAc
  4. washthe EtOAc layer was washed again with 3.7% HCl and saturated NaCl
  5. dry with materialOrganic layer was dried (MgSO4)
  6. customremoved in vacuo

Sources & evidence

ORD record
ord-f7bc257799294b278ce9f275360629a7
Source dataset
uspto-grants-1989_05
Patent number
US04835279

Reaction notes

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