Isopropanol → HCID 61101590, compound
Reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[O:6][CH2:7][CH2:8][O:9][C:4]=2[CH:3]=1.C([Li])CCC.[CH3:17][O:18][C:19]1[CH:26]=[CH:25][C:22]([CH:23]=[O:24])=[CH:21][CH:20]=1.C(O)(C)C>C1COCC1.O>[O:6]1[C:5]2[CH:10]=[CH:11][C:2]([CH:23]([C:22]3[CH:25]=[CH:26][C:19]([O:18][CH3:17])=[CH:20][CH:21]=3)[OH:24])=[CH:3][C:4]=2[O:9][CH2:8][CH2:7]1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -78 °C
Procedure
A stirred mixture of 6-bromo-2,3-dihydro-benzo[1,4]dioxine (1.66 g, 7.7 mmol) and dry THF (20 mL) was cooled to −78° C., evacuated and refilled with nitrogen for 10 cycles. To this clear solution was slowly added n-butyllithium (2.9 mL, 7.4 mmol) and stirred for 20 min. Then a mixture of 4-methoxy-benzaldehyde (0.90 g, 6.6 mmol) in dry THF (10 mL) was added and stirred for 1 hour at −78° C. The mixture was quenched with isopropanol (3.4 mL, 44 mmol) and added water (10 mL). The mixture was extracted with EtOAc (3×30 mL). The combined organic phases were washed with water (2×30 mL), dried over MgSO4 and concentrated to give (2,3-dihydro-benzo[1,4]dioxin-6-yl)-(4-methoxy-phenyl)-methanol as an oil (2.04 g, 102% crude yield). The product was used in the next step without further purification.
Workup
- customevacuated
- additionrefilled with nitrogen for 10 cycles
- additionwas added
- stirringstirred for 1 hour at −78° C
- extractionThe mixture was extracted with EtOAc (3×30 mL)
- washThe combined organic phases were washed with water (2×30 mL)
- dry with materialdried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-0e0c9477dbb6468aa214cb61671c73b4
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470723B2
Reaction notes
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