Oxetane, 3,3-bis(chloromethyl)- → HCID 86685334, compound
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)(=[O:4])=[O:3].C([Li])CCC.CN(C)CCN(C)C.Cl[CH2:25][C:26]1([CH2:30]Cl)[CH2:29][O:28][CH2:27]1>C1COCC1.O>[C:5]1([S:2]([CH:1]2[CH2:30][C:26]3([CH2:29][O:28][CH2:27]3)[CH2:25]2)(=[O:4])=[O:3])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Participants
Conditions
- Temperature
- -20 °C
Procedure
To a solution of methylsulfonylbenzene (2.00 g; 12.8 mmol) in dry THF (40 mL) under nitrogen at 0° C. was added butyl lithium (25.6 mmol; 2.5M solution on hexane). The mixture was stirred for 1 hour and then cooled to −20° C. Tetramethylethylenediamine (1.93 mL; 12.8 mmol) was added followed by a solution of 3,3-bis(chloromethyl)oxetane (1.98 g; 12.8 mmol) in dry THF (10 mL). The mixture was allowed to warm to 0° C. and then slowly allowed to reach 15° C. over 12 hours. Water (100 mL) was added and the mixture was extracted into ethyl acetate (4×50 mL). The combined extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The material was purified on silica gel (Biotage system, utilizing two 120 g columns in series) eluting with hexane/ethyl acetate (2:1 to 1:2 gradient). The desired product was obtained as an off white solid (700 mg).
Workup
- temperatureto warm to 0° C.
- waitto reach 15° C. over 12 hours
- extractionthe mixture was extracted into ethyl acetate (4×50 mL)
- dry with materialThe combined extracts were dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated under reduced pressure
- customThe material was purified on silica gel (Biotage system, utilizing two 120 g columns in series)
- washeluting with hexane/ethyl acetate (2:1 to 1:2 gradient)
Sources & evidence
- ORD record
- ord-45cc6aa1b7454537909f44a47537d5ca
- Source dataset
- uspto-grants-2015_02
- Patent number
- US08962596B2
Reaction notes
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