Dimethylformamide → {[3-(1,3-Dioxolan-2-yl)phenyl]ethynyl}-(trimethyl)silane

HRID 30549

반응식

HRID 30549 반응식
[C:1]([Si:3]([CH3:6])([CH3:5])[CH3:4])#[CH:2].Br[C:8]1[CH:9]=[C:10]([CH:14]2[O:18][CH2:17][CH2:16][O:15]2)[CH:11]=[CH:12][CH:13]=1.CN(C)C=O.C(N(CC)CC)C>[Cu](I)I.O>[O:15]1[CH2:16][CH2:17][O:18][CH:14]1[C:10]1[CH:9]=[C:8]([C:2]#[C:1][Si:3]([CH3:6])([CH3:5])[CH3:4])[CH:13]=[CH:12][CH:11]=1

참가 물질

7

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 873062-(3-Bromophenyl)-1,3-dioxolane

생성물 1

HCID 19897376{[3-(1,3-Dioxolan-2-yl)phenyl]ethynyl}-(trimethyl)silane수율 74.9%

시약·촉매·용매 2

HCID 83717Copper iodide촉매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

A mixture of ethynyl(trimethyl)silane (36 g, 367 mmol), 2-(3-bromophenyl)-1,3-dioxolane (78 g, 342 mmol), N,N-dimethylformamide (400 mL), and triethylamine (1.1 81 mL, mmol) was bubbled with anhydrous argon for 5 minutes, treated with copper iodide (0.94 g, 4.96 mmol) and dichlorobis(triphenylphosphine) palladium(II) (7.7 g, 11.01 mmol), stirred at 60° C. for 3 hours, cooled to room temperature, poured into water and extracted with ethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo to give {[3-(1,3-dioxolan-2-yl)phenyl]ethynyl}-(trimethyl)silane as a yellow oil (63 g, 256 mmol). The yellow oil was dissolved in MeOH (600 mL) and CH2Cl2 (600 mL), treated with cesium carbonate (91.8 g, 281.6 mmol), stirred at room temperature for 10 h, poured into water and extracted with ethyl ether. The ether extracts were combined, dried over MgSO4, concentrated in vacuo and distilled to give 2-(3-ethynylphenyl)-1,3-dioxolane as a yellow oil (42 g, 71% yield), MS m/e M+ 174; 1H NMR (400 MHz, DMSO-d6) 3.9-4.05 (m, 4H), 4.15 (s, 1H), 5.7 (s, 1H), 7.35-7.45 (m, 4H).

후처리

  1. customwas bubbled with anhydrous argon for 5 minutes
  2. temperaturecooled to room temperature
  3. extractionextracted with ethyl ether
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-edf0b5c159e345ddb1cb5a2483a44d0c
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07423158B2

연결된 노트

불러오는 중…