Sodium Bicarbonate → 1-(Phenylsulfanyl)-2-vinylbenzene

HRID 1893134노트

반응식

HRID 1893134 반응식
[I-].[CH3:2][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[C:28]1([S:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[CH:41]=O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C(=O)(O)[O-].[Na+]>CCOCC>[C:28]1([S:34][C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][C:36]=2[CH:41]=[CH2:2])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

참가 물질

6

반응물 4

HCID 516892Sodium BicarbonateHCID 638159Methyltriphenylphosphonium iodideHCID 123406852-(Phenylthio)benzaldehydeHCID 23665647Potassium tert-butoxide

생성물 1

HCID 128123101-(Phenylsulfanyl)-2-vinylbenzene

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

Methyl triphenylphosphonium iodide (1.57 g, 3.88 mmol) was dissolved in 25 mL ether in a 50 mL round-bottomed flask under dry nitrogen. To the mixture was added in one portion at 0° C. potassium tert-butoxide (0.47 g, 4.19 mmol) and it was stirred for 10 min at room temperature. 2-(phenylsulfanyl)benzenecarbaldehyde (2.77 mmol) was added in one portion at 0° C. and the reaction mixture was stirred until complete disappearance of the reactants (17 hr) at room temperature (followed by TLC). The mixture was added, to 50 mL of saturated sodium bicarbonate solution, followed by extraction with 3×50 mL portions of ether. The extracts were dried with magnesium sulfate and evaporated. The crude product was further purified by chromatography on silica gel using petroleum ether 60-80 as eluent. Yield: 0.53 g, 91%, colorless oil. 1H NMR (200 MHz, CDCl3): δ 5.33 (dd, J1=10.9, J2=1.2, 1H), 5.74 (dd, J1=17.4, J2=1.2, 1H), 7.16-7.65 (m, 10H) ppm.

후처리

  1. stirringthe reaction mixture was stirred until complete disappearance of the reactants (17 hr) at room temperature (followed by TLC)
  2. extractionfollowed by extraction with 3×50 mL portions of ether
  3. dry with materialThe extracts were dried with magnesium sulfate
  4. customevaporated
  5. customThe crude product was further purified by chromatography on silica gel

출처 및 근거

ORD 기록
ord-200b2421e409415b882ff95d4c6a2541
출처 데이터셋
uspto-grants-2013_08
특허 번호
US08513151B2

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