Triphenylphosphine → HCID 178443932, Verbindung

HRID 1603310Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1603310
CCOC(/N=N/C(OCC)=O)=O.[F:13][C@H:14]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[CH2:15][OH:16].[F:23][C:24]1[C:29]([F:30])=[C:28]([CH2:31][CH2:32][C@H:33]2[CH2:38][CH2:37][C@H:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:35][CH2:34]2)[CH:27]=[CH:26][C:25]=1[C:44]1[N:49]=[CH:48][C:47](O)=[CH:46][N:45]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.FC1C(F)=C(CCCCC)C=CC=1C1N=CC(OC[C@H](F)CCCCCC)=CN=1>C1COCC1>[F:23][C:24]1[C:29]([F:30])=[C:28]([CH2:31][CH2:32][C@H:33]2[CH2:34][CH2:35][C@H:36]([CH2:39][CH2:40][CH2:41][CH2:42][CH3:43])[CH2:37][CH2:38]2)[CH:27]=[CH:26][C:25]=1[C:44]1[N:45]=[CH:46][C:47]([O:16][CH2:15][C@H:14]([F:13])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:48][N:49]=1

Komponenten

7

Edukt 5

HCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 10855629(R)-(+)-2-fluorooctanolHCID 10993240HCID 10993240, VerbindungHCID 178444400HCID 178444400, Verbindung

Produkt 1

HCID 178443932HCID 178443932, VerbindungAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

--Quantities: DEAD (448 mg, 2.58 mmol) in THF (3 ml), (R)-(+)-2-fluorooctanol (379 mg, 2.58 mmol), hydroxypyrimidine 48 (1.0 g, 2.58 mmol), triphenylphosphine (676 mg, 2.58 mmol). The experimental procedure was as described for compound 34. The crude product was purified by flash chromatography (5 to 7% ethyl acetate-light petroleum) to give the 2-fluorooctyloxypyrimidine 49 (820 mg, 61%) (from EtOH), transitions/° C. K 102.2 N* 128.3 I; [α]D26 -2.4° (c 2.0 in CHCl3); νmax /cm-1 (KBr) 2920, 2845, 1540, 1460, 1435s, 1285 1085, and 900; δ 0.80-1.03 (10H, m), 1.06-1.45 (16H, m), 1.55 (4H, m), 1.82 (6H, m), 2.71 (2H, t J 8, ArCH2), 4.22 (2H, dd, 3JHF 22 and J 4, OCH2), 4.86 (1H, d of sext, 2JHF 48 and J 4, CHF), 7.01 (1H, ddd, J 7.5, 7 and 1.5, 5'-H), 7.67 (1H, ddd, J 7.5, 7 and 1.5, 5'-H) and 8.53 (2H, s, 4- and 6-H); m/z 518 (M+), 489, 475, 461, 447, 365 and 353.

Aufarbeitung

  1. customThe crude product was purified by flash chromatography (5 to 7% ethyl acetate-light petroleum)

Quellen und Nachweise

ORD-Eintrag
ord-baacf50b1cae426f934ced85b5e9df81
Quelldatensatz
uspto-grants-1999_11
Patentnummer
US05986096

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