Hydrochloric Acid → HCID 20549729, compound
Reaction equation
[CH2:1]([CH:3]1[O:7][C:6](=[O:8])[CH:5]([F:9])[CH2:4]1)[CH3:2].C1(C)C=CC=CC=1.CC(C[Al]CC(C)C)C.Cl>O1CCCC1>[CH2:1]([CH:3]1[O:7][CH:6]([OH:8])[CH:5]([F:9])[CH2:4]1)[CH3:2]Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -70 °C
Procedure
To a solution of 19.8 g (0.15 mol) of 5-ethyl-3-fluorodihydro-2(3H)-furanone dissolved in 500 ml of dry tetrahydrofuran was added at -70° C., 128 ml of a 1.4 M toluene solution of Dibal-H. The solution was stirred at -70° C. for one hour and then added cautiously to ice water. The resulting mixture was adjusted to pH~1 with 200 ml of 1 N hydrochloric acid and then extracted with methylene chloride. The solution was dried (MgSO4) and the solvent removed under reduced pressure to give 20 g of crude product. Distillation afforded 13.13 g of 5-ethyl-3-fluorotetrahydro-2-furanol: bp 45°-46° C. (0.1 mm Hg).
Workup
- additionwas added at -70° C.
- extractionextracted with methylene chloride
- dry with materialThe solution was dried (MgSO4)
- customthe solvent removed under reduced pressure
- customto give 20 g of crude product
- distillationDistillation
Sources & evidence
- ORD record
- ord-02cd9b2384db4dcfa8f8ceb02eeb2d39
- Source dataset
- uspto-grants-1982_03
- Patent number
- US04317775
Reaction notes
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