Hexane → 4-(1,3-Dioxolan-2-yl)-5-tributylstannylthiazole

HRID 6825

반응식

HRID 6825 반응식
Br[C:2]1[S:3][CH:4]=[C:5]([CH:7]2[O:11][CH2:10][CH2:9][O:8]2)[N:6]=1.C([Li])CCC.CCCCCC.[CH2:23]([Sn:27](Cl)([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH2:25][CH3:26]>C1COCC1.O>[O:8]1[CH2:9][CH2:10][O:11][CH:7]1[C:5]1[N:6]=[CH:2][S:3][C:4]=1[Sn:27]([CH2:28][CH2:29][CH2:30][CH3:31])([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:23][CH2:24][CH2:25][CH3:26]

참가 물질

7

반응물 4

HCID 8058HexaneHCID 15096Tributyltin ChlorideHCID 219522862-Bromo-4-(1,3-dioxolan-2-yl)thiazoleHCID 178418339Butyllithium

생성물 1

HCID 219520694-(1,3-Dioxolan-2-yl)-5-tributylstannylthiazole수율 98.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

2-Bromo-4-(1,3-dioxolan-2-yl) thiazole (6.4 g ,27.14 mmol) was stirred at −78° C. in dry THF (38 ml). 1.6M n butyl lithium in hexane (18.6 ml, 29.78 mmol) was added dropwise under nitrogen. After 30 min at this temperature, tributyl tin chloride (7.35 ml, 27.14 mmol) was added dropwise. The reaction was allowed to warm to 0° and water (20 ml) was added. The product was extracted into ether (3×100 ml). The combined organic extracts were dried (MgSO4 ) and evaporated. The residue was triturated with isohexane (3×100 ml) and the mother liquors were decanted, combined and concentrated to give a brown oil (11.88 g); m/z 444–450.

후처리

  1. temperatureto warm to 0°
  2. extractionThe product was extracted into ether (3×100 ml)
  3. dry with materialThe combined organic extracts were dried (MgSO4 )
  4. customevaporated
  5. customThe residue was triturated with isohexane (3×100 ml)
  6. customthe mother liquors were decanted
  7. concentrationconcentrated

출처 및 근거

ORD 기록
ord-8f9cade0188a4427a37fc2196adc5311
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07084147B2

연결된 노트

불러오는 중…