Tetrahydrofuran → 2,3-Dimethyl-2-butene
Reaction equation
[C:1]([BH2:7])([CH:4]([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:8]1[CH2:12][O:11][CH2:10][CH2:9]1>>[BH3:7].[CH2:8]1[CH2:12][O:11][CH2:10][CH2:9]1.[CH3:2][C:1](=[C:4]([CH3:6])[CH3:5])[CH3:3]Participants
4
Procedure
A 10 mL round-bottomed flask was charged with 5-carbon linked dimer alcohol (57 mg, 0.0885 mmol) in 1 mL of THF. To the reaction mixture was added thexylborane (0.8 mL, 3 eq.) 0.33M in THF solution obtained from BH3THF (1 eq) and 2,3-dimethyl-2-butene (2 eq) at 0° C. for 1 hr. The reaction mixture was stirred for 2 hr and then added 3 N NaOH (0.15 mL, 5 eq) and 30% H2O2 (0.15 mL, 5 eq). The reaction mixture was warmed to room temperature and then stirred for 12 hr. The reaction mixture was quenched with H2O, extracted with EtOAc, dried over MgSO4 and concentrated. The crude product was purified by column chromatography (EtOAc/Hexane=3/1) to give 39.2 mg in 65% yield.
Sources & evidence
- ORD record
- ord-bb61b7929eb245cab96fc434a5f22a00
- Source dataset
- uspto-grants-2014_11
- Patent number
- US08884032B2
Reaction notes
Loading…