tert-Butyl (triphenylphosphoranylidene) acetate → (E)t-Butyl 7-phenyl-2-heptenoate

HRID 381392

Reaktionsgleichung

Reaktionsgleichung von HRID 381392
[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10][CH:11]=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([O:17][C:18]([CH:20]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:19])([CH3:16])([CH3:15])[CH3:14]>O1CCCC1>[C:1]1([CH2:7][CH2:8][CH2:9][CH2:10]/[CH:11]=[CH:20]/[C:18]([O:17][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:19])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 561886Benzenepentanal

Produkt 1

HCID 10659015(E)t-Butyl 7-phenyl-2-heptenoateAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A stirred solution of 5-phenylpentanal (9.96 g, Reference Example 6) in anhydrous tetrahydrofuran (100 ml) at room temperature was treated with (tert-butoxycarbonylmethylene)triphenylphosphorane (27.5 g). The resulting orange solution was stirred for 2.5 hours then evaporated. The residual crude product was subjected to flash chromatography on silica eluting with a mixture of hexane and ethyl acetate (19:1, v/v) to afford the title compound (12.4 g) as a colourless oil. NMR (CDCl3): δ1.45 (s,9H), 1.65 (m,4H), 2.18 (q,2H), 2.61 (t,2H), 5.70 (d,1H), 6.82 (dt,1H), 7.10-7.30 (m,5H).

Aufarbeitung

  1. customthen evaporated
  2. additionThe residual crude product was subjected to flash chromatography on silica eluting with a mixture of hexane and ethyl acetate (19:1

Quellen und Nachweise

ORD-Eintrag
ord-eba8236c74a9422e9aa2c48de5d45be3
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06306873B1

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