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

HRID 1893134ノート

反応式

HRID 1893134 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 128123101-(Phenylsulfanyl)-2-vinylbenzene

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-200b2421e409415b882ff95d4c6a2541
出典データセット
uspto-grants-2013_08
特許番号
US08513151B2

反応ノート

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