Hexane → 5-Trimethylstannyl-4,4'-didodecyl-2,2'-bithiophene

HRID 1257981노트

반응식

HRID 1257981 반응식
Br[C:2]1[S:6][C:5]([C:7]2[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:11]=2)=[CH:4][C:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35].C([Li])CCC.CCCCCC.[CH3:47][Sn:48](Cl)([CH3:50])[CH3:49]>C1COCC1.C(OCC)C.O>[CH3:47][Sn:48]([CH3:50])([CH3:49])[C:2]1[S:6][C:5]([C:7]2[S:8][CH:9]=[C:10]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH:11]=2)=[CH:4][C:3]=1[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

참가 물질

8

반응물 4

HCID 8058HexaneHCID 14016Trimethyltin chlorideHCID 671208205-Bromo-4,4'-didodecyl-2,2'-bithiopheneHCID 178418339Butyllithium

생성물 1

HCID 575726935-Trimethylstannyl-4,4'-didodecyl-2,2'-bithiophene수율 90%

시약·촉매·용매 3

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매2회

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온도
-78 °C

실험 절차

To a solution of 5-bromo-4,4′-didodecyl-2,2′-bithiophene (29A, 100 mg, 0.172 mmol) in 4.0 mL of THF was added dropwise a solution of n-butyllithium in hexane (0.076 mL, 2.5 M, 0.189 mmol) at −78° C. The solution was stirred at −78° C. for 1 hour and a solution of trimethyltin chloride in THF (0.20 mL, 1.0 M, 0.20 mmol) was added in one portion. The solution was warmed to room temperature and 10.0 mL of water and 10.0 mL of diethylether were added. The organic layer was separated and washed twice with 20 mL of water and dried over magnesium sulfate. After filtration, the filtrate was concentrated in vacuo to yield 5-trimethylstannyl-4,4′-didodecyl-2,2′-bithiophene (29, 0.103 g, 90% yield) as a yellow oil. 1H NMR (CDCl3): δ 0.84-1.64 (m, 46H), 2.58 (m, 4H), 6.77 (s, 1H), 6.99 (s, 1H), 7.13 (s, 1H).

후처리

  1. temperatureThe solution was warmed to room temperature
  2. customThe organic layer was separated
  3. washwashed twice with 20 mL of water
  4. dry with materialdried over magnesium sulfate
  5. filtrationAfter filtration
  6. concentrationthe filtrate was concentrated in vacuo

출처 및 근거

ORD 기록
ord-cb0ead2b64da435eb05658c051c743c5
출처 데이터셋
uspto-grants-2013_06
특허 번호
USRE044304E1

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