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

HRID 453303

반응식

HRID 453303 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-0ad35b83c5b34879b8cb1546773de64f
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08492401B2

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