Aluminium lithium hydride → 2-(hydroxymethyl)-3,4-dihydronaphthalen-1(2H)-one
Reaction equation
C[O:2][C:3]([C:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][C:9](CC(C)(C)C)=[CH:10][CH:11]=2)[C:6]=1[OH:20])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:2][CH2:3][CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:6]1=[O:20]Participants
Conditions
- Temperature
- 0 °C
Procedure
To an ice-cooled solution of 7-(2,2-Dimethyl-propyl)-1-hydroxy-3,4-dihydro-naphthalene-2-carboxylic acid methyl ester (2.49 g, 9.07 mmol) in tetrahydrofuran (20 mL) was added lithium aluminum hydride (1 M in tetrahydrofuran, 9 mL, 9 mmol). The reaction mixture was stirred at 0° C. for 2 h and then quenched with saturated ammonium chloride and ethyl acetate. The resulting emulsion was filtered through diatomaceous earth. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined extracts were washed with saturated sodium chloride, dried (sodium sulfate), filtered, and concentrated under reduced pressure. Flash column chromatography (silica gel, 10-20% ethyl acetate/hexanes) provided hydroxymethyl tetralone (1.55 g, 70%): 1H NMR (300 MHz, CDCl3) δ 7.78 (d, J=1.4 Hz, 1H), 7.27 (dd, J=7.8, 1.4 Hz, 1H), 7.16 (d, J=7.8 Hz, 1H), 4.00-3.90 (m, 1H), 3.85-3.75 (m, 1H), 3.20-3.10 (m, 1H), 3.08-2.90 (m, 2H), 2.75-2.60 (m, 1H), 2.52 (s, 2H), 2.15-2.05 (m, 1H), 2.00-1.85 (m, 1H), 0.90 (s, 9H).
Workup
- customquenched with saturated ammonium chloride and ethyl acetate
- filtrationThe resulting emulsion was filtered through diatomaceous earth
- customThe organic layer was separated
- extractionthe aqueous layer was extracted with ethyl acetate
- washThe combined extracts were washed with saturated sodium chloride
- dry with materialdried (sodium sulfate)
- filtrationfiltered
- concentrationconcentrated under reduced pressure
Sources & evidence
- ORD record
- ord-e8a7ba42915c4cfd8acfb95f87fdd903
- Source dataset
- uspto-grants-2009_06
- Patent number
- US07544717B2
Reaction notes
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