Tetrabutylammonium Fluoride Trihydrate → 3-Hydroxy-9H-xanthen-9-ylideneadamantane

HRID 1088481Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1088481
[Si]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13](=[C:23]3[CH:30]4[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:32][CH:24]3[CH2:25]5)[CH2:29]4)[C:14]3[C:19]([O:20][C:21]=2[CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3)(C(C)(C)C)(C)C.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-].O.O.O>C1COCC1.CCOCC>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:13](=[C:23]3[CH:30]4[CH2:31][CH:26]5[CH2:27][CH:28]([CH2:32][CH:24]3[CH2:25]5)[CH2:29]4)[C:14]3[C:19]([O:20][C:21]=2[CH:22]=1)=[CH:18][CH:17]=[CH:16][CH:15]=3

Komponenten

5

Edukt 2

HCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 14645572HCID 14645572, Verbindung

Produkt 1

HCID 146455733-Hydroxy-9H-xanthen-9-ylideneadamantaneAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The silylated alkene 5b (1.18 g, 2.6 mmol) was dissolved in 10 ml of THF. n-Bu4NF·3H2O (0.94 g, 3.0 mmol) was added and the yellow solution stirred for 30 min. The solution was then diluted with Et2O (100 mL), washed with H2O (200 mL), and the organic layer was concentrated. Recrystallization from ethyl acetate gave 0.48 g (1.5 mmol, 57.7%) of 5a as a white solid: 235°-240° C. (dec); 1H NMR (CDCl3) delta 1.873 (2, 10H), 1.992 (s, 2H), 3.472 (s, 1H), 3.529 (s, 1H), 6.70-6.76 (m, 2H), 6.96-7.04 (m, 2H), 7.06-7.14 (m, 2H), 7.21-7.29 (m, 2H); HRMS calc. 330.1621, found 330.1617; MS m/e (rel. intensity) 330 (100), 329 (43), 273 (37), 235 (16), 197 (11), 142 (65). Anal. calcd for C23H22O2 : C, 83.64; H, 6.67. Found; C, 83.75; H, 6.69. ##STR40##

Aufarbeitung

  1. washwashed with H2O (200 mL)
  2. concentrationthe organic layer was concentrated
  3. customRecrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-73968ce5009b49a4b8255ae89cdfbf16
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04962192

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