1-[(3-Buten-1-yl)diphenylsilyl]-3-methyl-1-butanone → 1-[(3-Buten-1-yl)diphenylsilyl]-3-methyl-1-butanol

HRID 8541Notes

Reaction equation

HRID 8541 reaction equation
[CH2:1]([Si:5]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6](=[O:11])[CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:2][CH:3]=[CH2:4].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C>[CH2:1]([Si:5]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH:6]([OH:11])[CH2:7][CH:8]([CH3:10])[CH3:9])[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 153498501-[(3-Buten-1-yl)diphenylsilyl]-3-methyl-1-butanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 220158361-[(3-Buten-1-yl)diphenylsilyl]-3-methyl-1-butanolYield 69.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 33 (3.0 g, 9.3 mmol) in ethyl ether (100 mL) at 0° C. was added lithium aluminum hydride (1.0 M in ethyl ether, 47 mmol). After stirring for 15 min at 0° C. under argon, the reaction mixture was diluted with ethyl ether (300 mL) and quenched with saturated aqueous Na2SO4 until evolution of hydrogen had ceased. The mixture was dried with solid Na2SO4 and filtered, and the residue was extracted with ether (50 mL). The organic extracts were combined and concentrated in vacuo. Flash chromatography over silica gel (1/9 EtOAc:hexane) gave pure 34 as a colorless oil (2.1 g, 69%): Rf=0.60 (1/9 EtOAc:hexane); 1H NMR (300 MHz, CDCl3) δ 7.57 (m, 4H), 7.37 (m, 6H), 5.87 (m, 1H), 4.97 (dd. J=17.11.7 Hz, 1H), 4.88 (dd, J=102, 1.7 Hz, 1H), 4.08 (d, J=12.1 Hz, 1H), 2.12 (m, 2H), 1.85 (m, 1H), 1.58 (m, 1H), 1.26 (m, 4H), 0.88 (d, J=6.2 Hz, 6H); 13C NMR (75 MHz, CDCl3) δ 141.4, 135.7, 133.8, 129.8, 128.2, 113.3, 61.5, 42.4, 27.5, 24.2, 23.7, 20.7, 9.8; IR (neat) 3565 (m), 3452 (m, br), 3069 (m), 3050 (m), 2955 (s), 2910 (s), 2869 (m), 1965 (w), 1894 (w), 1832 (w), 1642 (m), 1469 (m), 1434 (s), 1369 (w), 1116 (s), 1001 m), 916 (m), 743 (s), 705 (s) cm−1; MS (FAB) m/e (rel. intensity) 323 (MH+-2, 5), 269 (21), 238 (11), 198 (57), 1.83 (100), 181 (10), 177 (23), 161 (14) 159 (56), 123 (15), 99 (12); HRMS (FAB) calcd for C21H27OSi: 323.1831 (MH+-2), found: 323.1824. Anal. Calcd for C21H28SiO: C, 77.72; H, 8.70. Found: C, 77.60; H, 8.67.

Workup

  1. customquenched with saturated aqueous Na2SO4 until evolution of hydrogen
  2. dry with materialThe mixture was dried with solid Na2SO4
  3. filtrationfiltered
  4. extractionthe residue was extracted with ether (50 mL)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dc0c6a839ea34b48b84ba6911f804829
Source dataset
uspto-grants-2006_08
Patent number
US07087776B2

Reaction notes

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