Tetrahydrofuran → Hydrochloric Acid
Reaction equation
[Li].[Cl:2][C:3]1([CH3:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.C1C[O:12]CC1>>[Cl:2][C:3]1([CH3:8])[CH2:7][CH2:6][CH2:5][CH2:4]1.[CH3:8][C:3]1([OH:12])[CH2:7][CH2:6][CH2:5][CH2:4]1.[ClH:2]Participants
Conditions
- Temperature
- 0 °C
Procedure
To lithium sand (0.44 g, 63.0 mmol) in THF (100 mL) at 0° C. under argon was added 4,41-di-tert-butylbiphenyl (13.27 g, 51.0 mmol) and the resulting mixture was stirred at 0° C. overnight. The mixture was then cooled to −78° C. and 1-chloro-1-methylcyclopentane (3.0 g, 25.3 mmol) in THF (25 mL) was added. [1-Chloro-1-methylcyclopentane, a clear oil with b.p. 87-88° C./15T was obtained by the chlorination of 1-methylcyclopentanol with HCl gas.] This mixture was stirred for 15 min and the compound of Example g (5.34 g, 25.3 mmol) was added. The resulting solution was stirred at −78° C. for 1 h before being poured into water (250 mL). The aq layer was extracted three times with ether, and the combined extracts were dried (MgSO4) and concentrated to yield 2-[2-fluoro-6-(1-methyl-cyclopentyl)phenyl]-4,5-dihydro-4,4-dimethyloxazole, as a clear oil in 40% yield. This oxazoline was carried through Steps 1-4 of Example 90. The resulting final product was recrystallized from ether/hexanes and obtained as a white solid. m.p. 116-117° C.
Workup
- temperatureThe mixture was then cooled to −78° C.
Sources & evidence
- ORD record
- ord-0b13b3bc6b4d4e9caa208331b758a22a
- Source dataset
- uspto-grants-2002_06
- Patent number
- US06410558B1
Reaction notes
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