Hexane → 1-[6-(4-tert-Butyl-cyclohexyloxy)-naphthalen-2-yl]-ethanone
Reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:12][CH:13]3[CH2:18][CH2:17][CH:16]([C:19]([CH3:22])([CH3:21])[CH3:20])[CH2:15][CH2:14]3)[CH:8]=2)[CH:3]=1.C([Li])CCC.CCCCCC.CON(C)[C:37](=[O:39])[CH3:38]>C1COCC1>[C:19]([CH:16]1[CH2:15][CH2:14][CH:13]([O:12][C:7]2[CH:8]=[C:9]3[C:4](=[CH:5][CH:6]=2)[CH:3]=[C:2]([C:37](=[O:39])[CH3:38])[CH:11]=[CH:10]3)[CH2:18][CH2:17]1)([CH3:20])([CH3:21])[CH3:22]Participants
Conditions
- Temperature
- -78 °C
Procedure
To a solution of 2-Bromo-6-(4-tert-butyl-cyclohexyloxy)-naphthalene (5 g, 0.01 mol) in 15 mL dry THF stirring at −78° C., was added 2.0 M of n-Butyllithium in hexane (8.3 mL, 0.017 mol) dropwise. The reaction was then stirred at −78° C. for 15 minutes, yellow color results. N-Methoxy-N-methyl-acetamide (1.6 mL, 0.015 mol) in 5 mL THF was then added dropwise while the reaction was stirred at −78° C. (r×n went colorless upon addition of B). Reaction was then quenched with water and extracted three times with ethyl ether. Organics were dried over MgSO4, filtered, and concentrated to dryness under reduced pressure. Material was purified via column chromatography using a gradient of 0-10% EtOAC/Hexanes (ran neat hexanes for 5 min to elute desbromo SM) on 125 g of SiO2 to give the title compound as a white solid.
Workup
- customyellow color results
- stirringwas stirred at −78° C. (r×n
- additionwent colorless upon addition of B)
- customReaction
- customwas then quenched with water
- extractionextracted three times with ethyl ether
- dry with materialOrganics were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated to dryness under reduced pressure
- customMaterial was purified via column chromatography
- customa gradient of 0-10% EtOAC/Hexanes (ran neat hexanes for 5 min to elute desbromo SM)
Sources & evidence
- ORD record
- ord-d4e8c558dd79499fae24050244bc0f03
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802659B2
Reaction notes
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