Hydrochloric Acid → Methyl (+/-)-3-(5-methylthiazol-2-yl)-4-(4-benzyloxyphenyl)butanoate

HRID 1816000Notes

Reaction equation

HRID 1816000 reaction equation
[CH3:1][C:2]1[S:6][C:5](/[C:7](/[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2OCC2C=CC=CC=2)=[CH:8]\[C:9]([O:11][CH2:12]C)=[O:10])=[N:4][CH:3]=1.[Mg].Cl.[CH3:31][OH:32]>>[CH3:1][C:2]1[S:6][C:5]([CH:7]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:32][CH2:31][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:19][CH:20]=2)[CH2:8][C:9]([O:11][CH3:12])=[O:10])=[N:4][CH:3]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 5462224MagnesiumHCID 86759663Ethyl (+/-)-3-(5-methylthiazol-2-yl)-4-(benzyloxyphenyl)crotonate

Product 1

HCID 86759662Methyl (+/-)-3-(5-methylthiazol-2-yl)-4-(4-benzyloxyphenyl)butanoate

Procedure

Ethyl (±)-3-(5-methylthiazol-2-yl)-4-(benzyloxyphenyl)crotonate (0.99 mmole, crude) was dissolved in MeOH (5 mL), and magnesium turnings (120 mg, 4.95 mmole) were added at RT. After 72 hr the mixture was poured into 10% HCl (75 mL) and extracted with CH2Cl2 (3×50 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated to afford the crude title compound. This was used without purification: MS (ES) m/e 382 (M+H)+.

Workup

  1. extractionextracted with CH2Cl2 (3×50 mL)
  2. dry with materialThe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-381ccaf6a9eb4314a9cbdd68ad45058f
Source dataset
uspto-grants-2005_04
Patent number
US06881736B1

Reaction notes

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