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

HRID 47988Notes

Reaction equation

HRID 47988 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-b127804087c343f9bbe581ebcf12d4f9
Source dataset
uspto-grants-2004_03
Patent number
US06699910B2

Reaction notes

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