Tert-Butyl hypochlorite → HCID 23356090, compound
Reaction equation
C(O[Cl:6])(C)(C)C.[CH2:7]([O:9][C:10]([CH:12]1[CH2:21][C:20]2[C:15](=[C:16]([O:24][CH3:25])[CH:17]=[CH:18][C:19]=2[O:22][CH3:23])[CH2:14][O:13]1)=[O:11])[CH3:8]>C(Cl)Cl>[CH2:7]([O:9][C:10]([CH:12]1[CH2:21][C:20]2[C:15](=[C:16]([O:24][CH3:25])[C:17]([Cl:6])=[CH:18][C:19]=2[O:22][CH3:23])[CH2:14][O:13]1)=[O:11])[CH3:8]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Under argon and at room temperature, was added dropwise 0.820 g (7.6 mmol) of t-butylhypochlorite to a stirred solution containing 1.973 g (7.4 mmol) of the isochroman from step 5 in 75 ml of anhydrous CH2Cl2. The reaction mixture was stirred for 3 hours and then washed successively with 25 ml portions of saturated aqueous sodium thiosulfate, water and brine. After drying over Na2SO4, the organic layer was evaporated and the residue was flash chromatographed with 2.5% ethyl acetate in toluene as the eluting solvent mixture. The title compound was obtained in 46% yield (1.02 g). (MP: 95.0° C.) 1H NMR (200 MHz, CDCl3) δ: 1.35 (t, 3H, J=7.1 Hz, CH3), 2.93 (broad dd, J=16.8, 10.3 Hz, HCHaCHC=O), 3.16 (broad dd, J=16.9, 3.2 Hz, HCHeCHC=O), 3.78 (s, 3H, OCH3), 3.81 (s, 3H, OCH3), 4.27 (dd, J=10.2, 3.3 Hz, --CH), 4.31 (q, 2H, J=7.1Hz, OCH2), 4.63 (broad d, 1H, J=16.2 Hz, HCHa0), 5.01 (d, 1H, J=16.2 Hz, HCHe0), 6.73 (s, 1H, ArH).
Workup
- washwashed successively with 25 ml portions of saturated aqueous sodium thiosulfate, water and brine
- dry with materialAfter drying over Na2SO4
- customthe organic layer was evaporated
- customchromatographed with 2.5% ethyl acetate in toluene as the eluting solvent mixture
Sources & evidence
- ORD record
- ord-d34adf19820441419ed16c20627d183a
- Source dataset
- uspto-grants-1997_01
- Patent number
- US05593970
Reaction notes
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