Sodium Bicarbonate → Ethyl 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylate

HRID 453303Notes

Reaction equation

HRID 453303 reaction equation
[Br-].[O:2]1[CH2:6][CH2:5][O:4][CH:3]1[CH2:7][CH2:8][Zn+].Br[C:11]1[S:15][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:13][C:12]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23].C([O-])(O)=O.[Na+]>C1COCC1>[O:2]1[CH2:6][CH2:5][O:4][CH:3]1[CH2:7][CH2:8][C:11]1[S:15][C:14]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:13][C:12]=1[C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 44558337Ethyl 5-bromo-2-phenylthiazole-4-carboxylateHCID 178419780HCID 178419780, compound

Product 1

HCID 67434696Ethyl 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylateYield 52.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A THF solution of (2-(1,3-dioxolan-2-yl)ethyl)zinc(II) bromide (35 mL, 17.3 mmol) was added to a degassed solution of ethyl 5-bromo-2-phenylthiazole-4-carboxylate (3.6 g, 11.5 mmol) and tetrakistriphenylphosphine palladium (666 mg, 0.58 mmol) in THF (20 mL). The reaction mixture was heated at reflux for 16 h then poured into sat aq NaHCO3. The mixture was extracted with EtOAc, washed with brine, dried (MgSO4), and concentrated. The crude product was purified by MPLC eluting with pentane/EtOAc (0-100% gradient) to give ethyl 5-(2-(1,3-dioxolan-2-yl)ethyl)-2-phenylthiazole-4-carboxylate (2.0 g, 52% yield).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. additionthen poured
  4. extractionThe mixture was extracted with EtOAc
  5. washwashed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe crude product was purified by MPLC
  9. washeluting with pentane/EtOAc (0-100% gradient)

Sources & evidence

ORD record
ord-0ad35b83c5b34879b8cb1546773de64f
Source dataset
uspto-grants-2013_07
Patent number
US08492401B2

Reaction notes

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