Triphenylphosphine → (S)-methyl 1-(pent-4-en-2-yloxy)-2-naphthoate

HRID 921218

Reaktionsgleichung

Reaktionsgleichung von HRID 921218
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].[CH3:16][C@@H:17](O)[CH2:18][CH:19]=[CH2:20].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(/C(OCC)=O)=N/C(OCC)=O>C1COCC1>[CH3:20][C@H:19]([O:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13])[CH2:18][CH:17]=[CH2:16]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 703582-Naphthalenecarboxylic acid, 1-hydroxy-, methyl esterHCID 5354216Diethyl azodicarboxylate, (Z)-HCID 6999724(2R)-pent-4-en-2-ol

Produkt 1

HCID 118307160(S)-methyl 1-(pent-4-en-2-yloxy)-2-naphthoateAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of methyl 1-hydroxy-2-naphthoate (500 mg, 2.473 mmol), (R)-pent-4-en-2-ol (0.382 mL, 3.71 mmol), triphenylphosphine (1297 mg, 4.95 mmol) and (Z)-diethyl diazene-1,2-dicarboxylate (0.836 mL, 4.95 mmol) in THF (20 mL) was stirred at rt for 3 h. It was then concentrated and the residue was purified by biotage, eluting with 10% EtOAc/hexane to isolate (S)-methyl 1-(pent-4-en-2-yloxy)-2-naphthoate (500 mg, 74.8%) as an oil. 1H NMR (400 MHz, CDCl3) δ 8.41-8.27 (m, 1H), 7.96-7.81 (m, 2H), 7.69-7.45 (m, 3H), 5.89 (ddt, J=17.2, 10.1, 7.1 Hz, 1H), 5.22-5.04 (m, 2H), 4.49-4.29 (m, 1H), 3.99 (s, 3H), 2.66-2.57 (m, 1H), 2.55-2.46 (m, 1H), 1.28 (d, J=6.4 Hz, 3H).

Aufarbeitung

  1. concentrationIt was then concentrated
  2. customthe residue was purified by biotage
  3. washeluting with 10% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-2f9c33b311b1474ba6ffe53a4c34d604
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273067B2

Verknüpfte Notizen

Wird geladen…