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Aluminium lithium hydride → 2,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-([1,3]dithianyl)-tridecane-1,13-diol

HRID 47988
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Reaktionsgleichung

Reaktionsgleichung von HRID 47988
C([O:3][C:4](=O)[C:5]([C:39]1[CH:44]=[CH:43][C:42]([CH2:45][CH:46]([CH3:48])[CH3:47])=[CH:41][CH:40]=1)([CH3:38])[CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([CH:32]1[S:37][CH2:36][CH2:35][CH2:34][S:33]1)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=1)([CH3:21])[C:16](OCC)=[O:17])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH2:45]([C:42]1[CH:43]=[CH:44][C:39]([C:5]([CH3:38])([CH2:6][CH2:7][CH2:8][CH2:9][CH:10]([CH:32]2[S:33][CH2:34][CH2:35][CH2:36][S:37]2)[CH2:11][CH2:12][CH2:13][CH2:14][C:15]([C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH:29]([CH3:31])[CH3:30])=[CH:24][CH:23]=2)([CH3:21])[CH2:16][OH:17])[CH2:4][OH:3])=[CH:40][CH:41]=1)[CH:46]([CH3:48])[CH3:47]
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Komponenten

4

Edukt 2

HCID 21226445Aluminium lithium hydrideHCID 865877332,12-Bis-(4 isobutylphenyl)-2,12-dimethyl-7-([1,3]dithianyl)-tridecanedioic acid diethyl ester

Produkt 1

HCID 234314492,12-Bis-(4-isobutylphenyl)-2,12-dimethyl-7-([1,3]dithianyl)-tridecane-1,13-diolAusbeute 94 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

2,12-Bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-([1,3]dithianyl)-tridecanedioic acid diethyl ester (5.81 g, 8.33 mmol) was dissolved in freshly distilled tetrahydrofuran (THF, 50 mL) and added to lithium aluminum hydride (1.0 g, 26.3 mmol) in THF (50 mL) at −78° C. under a nitrogen atmosphere. The solution was warmed to room temperature over four hours. The reaction was then cooled back to −78° C. and quenched with ethyl acetate (5.0 mL). After warming to room temperature, water (100 mL) was added and the product was extracted with diethyl ether (2×100 mL). The ether extracts were combined, dried with sodium sulfate, filtered, and concentrated. After drying under high vacuum for four hours, the reaction yielded 2,12-bis-(4-isobutyl-phenyl)-2,12-dimethyl-7-([1,3]dithianyl)-tridecane-1,13-diol (4.80 g, 94% yield) as a colorless oil. 1H NMR (300 MHz, CDCl3/TMS): δ (ppm) 7.20 (d, 4H, J=8.0 Hz), 7.09 (d, 4H, J=8.0 Hz), 3.64 (d, 2H, J=10.7 Hz), 3.48 (d, 2H, J=10.7 Hz), 2.71 (t, 4H, J=5.1 Hz), 2.50-2.35 (m br., 2H), 2.43 (d, 4H, J=7.0 Hz), 1.90-1.80 (m, 4H), 1.80-1.68 (m, 6H), 1.58-1.42 (m, 2H), 1.38-1.25 (m, 4H), 1.30 (s, 6H), 1.26-1.10 (m, 2H), 1.10-0.95 (m, 2H), 0.89 (d, 12H, J=6.6 Hz). 13C NMR (75 MHz, CDCl3/TMS): δ (ppm) 141.94, 139.39, 129.20, 126.44, 72.48, 53.30, 44.97, 43.09, 38.45, 38.18, 30.21, 26.01, 25.64, 24.84, 24.09, 22.55, 21.64. HRMS (LSIMS, nba): Calcd. for C38H61O2S2 (MH+): 613.4113, found: 613.407.

Aufarbeitung

  1. temperatureThe reaction was then cooled back to −78° C.
  2. customquenched with ethyl acetate (5.0 mL)
  3. temperatureAfter warming to room temperature
  4. additionwater (100 mL) was added
  5. extractionthe product was extracted with diethyl ether (2×100 mL)
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customAfter drying under high vacuum for four hours

Quellen und Nachweise

ORD-Eintrag
ord-b127804087c343f9bbe581ebcf12d4f9
Quelldatensatz
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06699910B2

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