Ethyl Acetate → HCID 118307019, compound
Reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[C:4]([O:12][C@H:13]([CH2:15][CH:16]=[CH2:17])[CH3:14])[CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.[NH4+].[Cl-]>C1COCC1>[CH3:1][C:2]1[CH:11]=[CH:10][C:5]([CH2:6][OH:7])=[C:4]([O:12][C@H:13]([CH2:15][CH:16]=[CH2:17])[CH3:14])[CH:3]=1Participants
Conditions
- Temperature
- 0 °C
Procedure
(S)-Methyl 4-methyl-2-(pent-4-en-2-yloxy)benzoate (1 g, 4.27 mmol) was dissolved in THF and cooled to 0° C. To this was added lithium aluminum hydride (0.162 g, 4.27 mmol) and the reaction stirred 5 h at room temp. The mixture was cooled to 0° C. and ethyl acetate added, after which it was stirred for 15 min. Sat'd NH4Cl was added and the ice bath removed. Stirring was continued for 0.5 h then the mixture was transferred to a separatory funnel. The solution was extracted with ethyl acetate then dried over Na2SO4. After filtration the solvent was removed under vacuum. The crude product was purified by silica gel chromatography using a Biotage apparatus to provided 915 mg of the title compound as an oil. 1H NMR (400 MHz, DMSO) δ 1.22 (3H, d), 2.28 (3H, s), 2.37 (2H, m), 4.44 (2H, d), 4.50 (1H, m), 5.09 (2H, m), 5.86 (1H, m), 6.72 (1H, d0, 6.77 (1H, s), 7.24 (1H, d).
Workup
- temperatureThe mixture was cooled to 0° C.
- stirringafter which it was stirred for 15 min
- customthe ice bath removed
- stirringStirring
- waitwas continued for 0.5 h
- customthe mixture was transferred to a separatory funnel
- extractionThe solution was extracted with ethyl acetate
- dry with materialthen dried over Na2SO4
- filtrationAfter filtration the solvent
- customwas removed under vacuum
- customThe crude product was purified by silica gel chromatography
Sources & evidence
- ORD record
- ord-0a771f503bee43819d62e896c9cd3dd3
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273067B2
Reaction notes
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