Triphenylphosphine → 6-[(3,3-Difluorocyclobutyl)methoxy]-2,3-dihydro-1H-inden-1-one

HRID 1468069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1468069
[OH:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.[F:12][C:13]1([F:19])[CH2:16][CH:15]([CH2:17]O)[CH2:14]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1COCC1>[F:12][C:13]1([F:19])[CH2:16][CH:15]([CH2:17][O:1][C:2]2[CH:10]=[C:9]3[C:5]([CH2:6][CH2:7][C:8]3=[O:11])=[CH:4][CH:3]=2)[CH2:14]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 70206596-Hydroxy-1-indanoneHCID 45480377(3,3-Difluorocyclobutyl)methanol

Produkt 1

HCID 867067186-[(3,3-Difluorocyclobutyl)methoxy]-2,3-dihydro-1H-inden-1-oneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 6-hydroxy-2,3-dihydro-1H-inden-1-one (3.6 g, 24.3 mmol) in THF (60 mL) were (3,3-difluorocyclobutyl)methanol (2.97 g, 24.3 mmol) and triphenylphosphine (9.56 g, 36.45 mmol) added. Diisopropyl azodicarboxylate (7.18 mL, 36.5 mmol) was added dropwise. The reaction mixture was stirred at r.t. overnight. The material was purified by flash column chromatography using a gradient of 0-100% EtOAc in heptane, providing 3.67 g (60% yield) of the title compound. 1H NMR (500 MHz, DMSO-d6) ppm 2.30 (br. s., 1H) 2.42-2.52 (m, 6H) 2.54-2.62 (m, 1H) 2.63-2.66 (m, 2H) 2.67-2.76 (m, 2H) 2.98-3.04 (m, 2H) 4.08 (d, 2H) 7.10 (d, 1H) 7.26 (dd, 1H) 7.48 (d, 1H); MS (ES+) m/z 253 [M+H]+.

Aufarbeitung

  1. additionadded
  2. customThe material was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-acb985c483774953a2b2e29df3e02d41
Quelldatensatz
uspto-grants-2015_04
Patentnummer
US09000185B2

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