Hydrochloric Acid → Ethyl 2-(3-isopentyl-4-oxo-2-phenylthiazolidin-5-ylidene)acetate

HRID 1695905Notes

Reaction equation

HRID 1695905 reaction equation
[CH2:1]([N:6]1[C:10](=[O:11])[CH2:9][S:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH:3]([CH3:5])[CH3:4].[Li+].CC([N-]C(C)C)C.[Li]CCCC.C(NC(C)C)(C)C.[C:38]([O:42][CH2:43][CH3:44])(=[O:41])[CH:39]=O.Cl>C1COCC1>[CH2:1]([N:6]1[C:10](=[O:11])[C:9](=[CH:39][C:38]([O:42][CH2:43][CH3:44])=[O:41])[S:8][CH:7]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2][CH:3]([CH3:5])[CH3:4]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 70211Ethyl oxoacetateHCID 2724682Lithium diisopropylamideHCID 59554952HCID 59554952, compoundHCID 178418339Butyllithium

Product 1

HCID 72325412Ethyl 2-(3-isopentyl-4-oxo-2-phenylthiazolidin-5-ylidene)acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 3-isopentyl-2-phenylthiazolidin-4-one (0.25 g, 1 mmol) in THF was added LDA (1.1 ml of ˜1 M in THF; freshly prepared from nBuLi and Diisopropylamine) at −78° C. and the reaction mixture was allowed to warm to room temperature. Ethyl glyoxalate (0.24 ml of ˜50% w/v in toluene, 1.2 mmol) was added and the reaction mixture was stirred at room temperature for 16 hours. The reaction mixture was poured into 1 N HCl and extracted with EtOAc (3×). The organics were combined, washed with brine, dried (MgSO4) and evaporated to dryness. Purification by column chromatography (5 to 15% EtOAc in Hx) gave the desired product as an oil.

Workup

  1. extractionextracted with EtOAc (3×)
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated to dryness
  5. customPurification by column chromatography (5 to 15% EtOAc in Hx)

Sources & evidence

ORD record
ord-d402e01e0af64dcd82f692fb7cfdea26
Source dataset
uspto-grants-2012_04
Patent number
US08163737B2

Reaction notes

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