Methanol → Methyl 3-(2-Isopropyl-4-thiazolyl)propanoate

HRID 2258246Notes

Reaction equation

HRID 2258246 reaction equation
[CH:1]([C:4]1[S:5][CH:6]=[C:7](/[CH:9]=[CH:10]/[C:11]([O:13][CH2:14]C)=[O:12])[N:8]=1)([CH3:3])[CH3:2].CO.[Mg].C(C1(CCC(OC)=O)NC=CS1)(C)C>C1COCC1>[CH:1]([C:4]1[S:5][CH:6]=[C:7]([CH2:9][CH2:10][C:11]([O:13][CH3:14])=[O:12])[N:8]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 887MethanolHCID 5462224Magnesium2×HCID 10727904Ethyl (2E)-3-[2-(1-methylethyl)-4-thiazolyl]-2-propenoateHCID 70012364Methyl 3-(2-isopropyl-4-thiazolinyl)propanoate

Product 1

HCID 18758926Methyl 3-(2-Isopropyl-4-thiazolyl)propanoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 225 mg (1 mmol) of (E)-ethyl 3-(2-isopropyl-4-thiazolyl)propenoate in 10 ml of freshly distilled (from calcium hydride) methanol and 1 ml of dry THF was treated with 49 mg (2 mmol) of magnesium turnings. The mixture was stirred for 20 min, during which the magnesium was consumed. The resulting solution was poured over cold aqueous HCl, basified to pH 8 with NaHCO3, extracted with ethyl acetate, dried over Na2SO4, and concentrated. Silica gel chromatography using 10% ethyl acetate in hexane provided a mixture of the desired compound and methyl 3-(2-isopropyl-4-thiazolinyl)propanoate.

Workup

  1. customwas consumed
  2. additionThe resulting solution was poured over cold aqueous HCl
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customprovided

Sources & evidence

ORD record
ord-e3b656e2d8f34adcbfada91b3ff00a93
Source dataset
uspto-grants-1997_08
Patent number
US05659045

Reaction notes

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