18-Crown-6 → 3-Benzo[b]thiophen-2-yl-acrylic acid tert-butyl ester

HRID 1013424

Reaktionsgleichung

Reaktionsgleichung von HRID 1013424
C[Si]([N-][Si](C)(C)C)(C)C.[K+].C1OCCOCCOCCOCCOCCOC1.[C:29]([O:33][C:34](=[O:52])[CH2:35]P(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O)([CH3:32])([CH3:31])[CH3:30].[S:53]1[C:57]([CH:58]=O)=[CH:56][C:55]2[CH:60]=[CH:61][CH:62]=[CH:63][C:54]1=2>C1COCC1>[C:29]([O:33][C:34](=[O:52])[CH:35]=[CH:58][C:57]1[S:53][C:54]2[CH:63]=[CH:62][CH:61]=[CH:60][C:55]=2[CH:56]=1)([CH3:32])([CH3:31])[CH3:30]

Komponenten

6

Edukt 4

HCID 2855718-Crown-6HCID 7365001-Benzothiophene-2-carbaldehydeHCID 3251421Potassium bis(trimethylsilyl)amideHCID 10689048Tert-butyl (diphenoxyphosphoryl)acetate

Produkt 1

HCID 672058673-Benzo[b]thiophen-2-yl-acrylic acid tert-butyl esterAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

Potassium bis(trimethylsilyl)amide (5.4 g, 0.027 mol) was added to a solution of 18-Crown-6 (13.7 g, 0.052 mol) and (diphenoxy-phosphoryl)-acetic acid tert-butyl ester (9.4 g, 0.027 mol) in dry THF (120 mL) at −78° C. After 30 minutes of stirring at this temperature, benzo[b]thiophene-2-carbaldehyde (4.0 g, 0.024 mol) was added and the reaction was stirred for 3 hours at −78° C. after which the reaction was quenched with saturated ammonium chloride (200 mL). The reaction mix was allowed to come to room temperature and was extracted with ethyl acetate (3×200 mL) and the combined organic extracts were washed with 10% HCl (200 mL), brine (200 mL), and dried over MgSO4. The solvent was evaporated in vacuo leaving the crude product that was purified by column chromatography (SiO2) using a 5-40% ethylacetate-hexane gradient to afford the subtitle compound (4.64 g, yield: 74%). MS calculated for C15H16O2S +H: 261, observed: 261.

Aufarbeitung

  1. additionwas added
  2. customwas quenched with saturated ammonium chloride (200 mL)
  3. additionThe reaction mix
  4. customto come to room temperature
  5. extractionwas extracted with ethyl acetate (3×200 mL)
  6. washthe combined organic extracts were washed with 10% HCl (200 mL), brine (200 mL)
  7. dry with materialdried over MgSO4
  8. customThe solvent was evaporated in vacuo
  9. customleaving the crude product that
  10. customwas purified by column chromatography (SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-50fe8b81151c4653a48db4325c88f59e
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07981919B2

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