Aluminium lithium hydride → [2-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalen-1-yl]methanol
Reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH2:17][CH2:18][CH:19]([CH3:21])[CH3:20])([C:13](OC)=[O:14])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[CH3:1][O:2][C:3]1[C:4]([CH2:13][OH:14])([CH2:17][CH2:18][CH:19]([CH3:20])[CH3:21])[C:5]2[C:10]([CH2:11][CH:12]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2Participants
Procedure
To a solution of Example 178A (0.3 g, 1 mmol) in tetrahydrofuran (5 mL) was added a 1.0 M solution of lithium aluminum hydride in tetrahydrofuran (1.2 mL, 1.2 mmol) dropwise. The solution was stirred at room temperature for 1 h and then quenched carefully with a saturated solution of NH4Cl (5 mL). The mixture was diluted with water (25 mL) and extracted with ethyl acetate (3× 15 mL). The combined organic extracts were dried (Na2SO4) and concentrated in vacuo. Column chromatography on silica (20% ethyl acetate/hexane) afforded product as a colorless oil (0.20 g, 74%). 1H NMR (300 MHz, CDCl3) δ ppm 0.79 (m, 8H), 1.37 (m, 1H), 1.55 (m, 1H), 1.98 (m, 1H), 3.53 (d, J=3.68 Hz, 2H), 3.63 (s, 3H), 3.71 (d, J=10.66 Hz, 1H), 3.95 (m, 1H), 5.09 (t, J=3.68 Hz, 1H), 7.22 (m, 4H); MS m/z 261.0 (M+H)+.
Workup
- customquenched carefully with a saturated solution of NH4Cl (5 mL)
- additionThe mixture was diluted with water (25 mL)
- extractionextracted with ethyl acetate (3× 15 mL)
- dry with materialThe combined organic extracts were dried (Na2SO4)
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-b8303bcf00ba4e81a33988f4df814e98
- Source dataset
- uspto-grants-2009_05
- Patent number
- US07538105B2
Reaction notes
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