tert-Butanol → 6-Bromo-2',3',5',6'-tetrahydrospiro[indene-2,4'-pyran]-1(3H)-one
Reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][CH2:7][C:8]2=[O:11])=[CH:4][CH:3]=1.C(O[K])(C)(C)C.CC(O)(C)C.Br[CH2:24][CH2:25][O:26][CH2:27][CH2:28]Br>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7]3([C:8]2=[O:11])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]3)=[CH:4][CH:3]=1Participants
6
Procedure
To a solution of 6-bromo-1-indanone (1.033 g, 4.89 mmol) in anhydrous THF (100 mL) under N2 atmosphere at room temperature was added a solution of tBuOK in tBuOH (1 M, 10.3 mL, 10.3 mmol) within 30 min (the color turned to deep black upon a drop of tBuOK solution was added), followed by 1-bromo-2-(2-bromoethoxy)ethane (1.134 g, 0.62 mL, 4.89 mmol). The reaction was quenched with saturated aqueous NH4Cl, and extracted with ether two times. The combined organic phases were washed with H2O, brine, and dried over anhydrous Na2SO4, and filtered, and concentrated to give black tar. It was purified by flash chromatography on silica gel yield 300 mg of the desired product. MS ESI+ve m/z 281 (M+H)30.
Workup
- additionwas added),
- customThe reaction was quenched with saturated aqueous NH4Cl
- extractionextracted with ether two times
- washThe combined organic phases were washed with H2O, brine
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- concentrationconcentrated
- customto give black tar
- customIt was purified by flash chromatography on silica gel yield 300 mg of the desired product
Sources & evidence
- ORD record
- ord-4ed081d750f344d0b8bc8cc8a8aeea7c
- Source dataset
- uspto-grants-2015_12
- Patent number
- US09212153B2
Reaction notes
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