Tetrahydrofuran → HCID 178471528, Verbindung

HRID 1975616Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1975616
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[CH2:13][CH2:12][CH:11]([CH:14]=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[OH-:16].[K+].[O:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1>O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:9][CH2:10][C@H:11](/[CH:14]=[CH:20]/[C:19]([O:18][CH2:22][CH3:21])=[O:16])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 8028TetrahydrofuranHCID 14797Potassium HydroxideHCID 190979014-(4-Bromophenyl)-cyclohexanecarboxaldehyde

Produkt 1

HCID 178471528HCID 178471528, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of 9.1 g of 4-(4-bromophenyl)cyclohexanecarb-oxaldehyde and 3.8 g of powdered potassium hydroxide in 200 ml of tetrahydrofuran was placed at room temperature in a sulphonation flask while gassing with argon and treated with 9.2 g of triethyl phosphonoacetate within 15 minutes, stirred overnight, taken up in 100 ml of water and extracted three times with 100 ml of methylene chloride each time. The organic phases were washed twice with 100 ml of water each time, dried over magnesium sulphate and concentrated. Low-pressure chromato-graphy of the residue (12 g) on silica gel with hexane/ethyl acetate (vol. 9:1) gave 11.7 g of ethyl (E)-3-[trans-4-(4-bromo-phenyl)cyclohexyl]acrylate as colourless crystals.

Aufarbeitung

  1. customwas placed at room temperature in a sulphonation flask
  2. extractionextracted three times with 100 ml of methylene chloride each time
  3. washThe organic phases were washed twice with 100 ml of water each time
  4. dry with materialdried over magnesium sulphate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-088a694ada344cf3aeb140b8ff18f938
Quelldatensatz
uspto-grants-1994_02
Patentnummer
US05288428

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