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Triethylamine → HCID 23501331, Verbindung

HRID 725706
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 725706
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(N(CC)CC)C.[Si:14]([O:21][C:22]1[CH:23]=[C:24]([CH:29]=[CH:30][CH:31]=1)[C:25]([O:27][CH3:28])=O)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15].[CH:32]12[CH2:41][CH:36]3[CH2:37][CH:38]([CH2:40][CH:34]([CH2:35]3)[C:33]1=O)[CH2:39]2>C1COCC1.CCOCC>[Si:14]([O:21][C:22]1[CH:23]=[C:24]([CH2:25][O:27][CH:28]=[C:33]2[CH:34]3[CH2:40][CH:38]4[CH2:37][CH:36]([CH2:41][CH:32]2[CH2:39]4)[CH2:35]3)[CH:29]=[CH:30][CH:31]=1)([C:17]([CH3:20])([CH3:19])[CH3:18])([CH3:16])[CH3:15]
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Komponenten

7

Edukt 4

HCID 8471TriethylamineHCID 64151AdamantanoneHCID 11715937Benzoic acid, 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-, methyl esterHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 23501331HCID 23501331, VerbindungAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A 500 mL three-neck flask was fitted with a reflux condenser, 125 mL addition funnel, and nitrogen line. The apparatus was dried by means of a hot air gun and nitrogen purging. Dry THF (200 mL) was added and the flask cooled in an ice bath. TiCL3 (24 g, 156 mmol) was added rapidly followed by LAH (2.8 g, 75 mmol) in portions with stirring. The cooling bath was removed and the black mixture was allowed to warm to room temperature. Triethylamine (12 mL, 86 mmol) was added to the stirred suspension and refluxed for 1 hour. After this period a solution of methyl 3-tert-butyldimethylsilyloxybenzoate (4.40 g, 16.6 mmol) and 2-adamantanone (3.0 g, 20.4 mmol) in 50 mL of dry THF was added dropwise to the refluxing mixture over 5 hours. Refluxing was continued for an additional 4 hours after which the reaction was cooled to room temperature and diluted with 100 mL of ether. The organic solution was separated and concentrated. Chromatography over silica with 1% ethyl acetate/hexane gave 1.29 g (21%) of 7b as an oil: 1H NMR (CDCl3) delta 0.196 (s, 6H), 0.985 (s, 9H), 1.78-1.97 (m, 12H), 2.628 (s, 1H, 3.23 (s, 1H), 3.29 (s, 3H), 6.75-7.20 (m, 4H); 13C NMR (CDCl3) delta -4.50, 18.19, 25.67, 28.37, 30.16, 32.28, 37.25, 38.19, 39.01, 57.51, 119.29, 121.08, 122.32, 128.87, 131.11, 136.84, 143.47, 155.37. ##STR45## Preparation of 1,2-Dioxetanes

Aufarbeitung

  1. customA 500 mL three-neck flask was fitted with a reflux condenser, 125 mL addition funnel
  2. customThe apparatus was dried by means of a hot air gun and nitrogen purging
  3. additionDry THF (200 mL) was added
  4. temperaturethe flask cooled in an ice bath
  5. additionTiCL3 (24 g, 156 mmol) was added rapidly
  6. customThe cooling bath was removed
  7. temperaturerefluxed for 1 hour
  8. temperatureRefluxing
  9. temperatureafter which the reaction was cooled to room temperature
  10. customThe organic solution was separated
  11. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-3b31509c2b7d498cad3e9015657d8355
Quelldatensatz
uspto-grants-1998_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05707559

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