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

HRID 6825

反応式

HRID 6825 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8f9cade0188a4427a37fc2196adc5311
出典データセット
uspto-grants-2006_08
特許番号
US07084147B2

関連ノート

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