Tributyltin Chloride → Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane

HRID 430735

반응식

HRID 430735 반응식
[CH2:1]1[O:9][C:8]2[C:4](=[CH:5][S:6][CH:7]=2)[O:3][CH2:2]1.[Li]CCCC.[Sn:15](Cl)([CH2:24][CH2:25][CH2:26][CH3:27])([CH2:20][CH2:21][CH2:22][CH3:23])[CH2:16][CH2:17][CH2:18][CH3:19]>C1COCC1>[CH2:24]([Sn:15]([CH2:16][CH2:17][CH2:18][CH3:19])([CH2:20][CH2:21][CH2:22][CH3:23])[C:5]1[S:6][CH:7]=[C:8]2[O:9][CH2:1][CH2:2][O:3][C:4]=12)[CH2:25][CH2:26][CH3:27]

참가 물질

5

반응물 3

HCID 15096Tributyltin ChlorideHCID 44218643,4-EthylenedioxythiopheneHCID 178418339Butyllithium

생성물 1

HCID 15891053Tributyl(2,3-dihydrothieno[3,4-b][1,4]dioxin-5-yl)stannane

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A structure of the product is depicted schematically in FIG. 13. To a cold (−15° C.) solution of 3,4-ethylenedioythiophene (EDOT) (20 ml, 188 mmol) in 350 mL of THF were slowly added 138 mL (207 mmol, 1.1 equiv) of nBuLi. The white slurry was allowed to stir at −15° C. for 3 h before the addition of 61.6 mL (227 mmol, 1.2 equiv) of Bu3SnCl. The beige slurry was allowed to stir while warming to room temperature for 18 h. The solvent was removed under vacuum and then stiffed in hexane for 30 min. The slurry was filtered through Celite and the amber filtrate was removed under vacuum to yield a yellow-orange oil which was purified by distillation (b.p. 120° C./30 mTorr) to yield 79.6 g (185, mmol 98%) of pale yellow oil. 1H NMR (CDCl3) δ6.57 (s, 1H), 4.20-4.10 (m, 4H), 1.62-1.50 (m, 6H), 1.40-1.25 (m, 6H), 1.12-1.06 (m, 6H), 0.89 (t, 3H). MS m/z 433 (M+H+); HRMS (FAB) m/z 433.1225 (M+H+); calcd for C18H32O2SSn m/z 433.1223 (M+H+).

후처리

  1. customThe solvent was removed under vacuum
  2. filtrationThe slurry was filtered through Celite
  3. customthe amber filtrate was removed under vacuum
  4. customto yield a yellow-orange oil which
  5. distillationwas purified by distillation (b.p. 120° C./30 mTorr)
  6. customto yield 79.6 g (185, mmol 98%) of pale yellow oil

출처 및 근거

ORD 기록
ord-82500da7314442d68968a70b0519e0e6
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06323309B1

연결된 노트

불러오는 중…