hex-5-en-1-ol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Following the general procedure of Example 13A, 5-hexenol was added to butadiene monoepoxide, using the following quantities of reagents and solvents: Pd2dba3.CHCl3 (5.2 mg, 5.0 μmol), (±)-8 (10.4 mg, 15 μmol), DMAP (6.2 mg, 50 μmol), a 1.0 M solution of Et3B in THF (5.0 μL, 5.0 μmol), 5-hexenol (240 μL, 2.0 mmol), butadiene monoepoxide (81 μL, 1.0 μmol), CH2Cl2 (10 mL). The reaction time in this case was 4 h. Flash chromatography of the crude material (silica gel, 4:1 pentane-ether) afforded ˜135 mg (80%) of a colorless oil. (enantiomers separated by chiral GLC, Cyclosil B column isothermal 120° C, (S)-(+)-isomerrt=15.52 min, (R)-(−)-isomerrt=16.21 min). 1H NMR (300 MHz) δ 1.36-1.43 (m, 2H), 1.50-1.58 (m, 2H), 1.97-2.04 (m, 2H), 2.50 (br s, 1H), 3.24-3.31 (m, 1H), 3.43-3.53 (m, 3H), 3.71-3.75 (m,1H), 4.89 (d, 1H, J=11 Hz), 4.94 (d, 1H, J=19Hz), 5.20 (d, 1H, J=9 Hz), 5.24 (d, 1H, J=17 Hz), 5.57-5.78 (m, 2H); 13C NMR (75.5 MHz) δ 25.3, 29.1, 33.4, 65.1, 68.6, 81.6, 114.5, 118.4, 135.4, 138.5. Anal. Calc'd. for C10H18O2: C, 70.55; H, 10.66. Found: C, 70.66; H, 10.43.

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-hexen-1-ol (900 mg, 9 mmol) and sodium hydride (310 mg, 9 mmol) in dry tetrahydrofuran was added a solution of 3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine (590 mg, 3 mmol) in dry tetrahydrofuran. The reaction mixture was stirred at room temperature for 1 h. Water was added and the mixture was extracted with ether. The ether phase was dried and evaporated to give the title compound. the mixture was extracted with ether The ether phase was dried evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-hexen-1-ol (900 mg, 9 mmol) and sodium hydride (310 mg, 9 mmol) in dry tetrahydrofuran was added a solution of 3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine (590 mg, 3 mmol) in dry tetrahydrofuran. The reaction mixture was stirred at room temperature for 1 h. Water was added and the mixture was extracted with ether. The ether phase was dried and evaporated to give the title compound. the mixture was extracted with ether The ether phase was dried evaporated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-hexen-1-ol (900 mg, 9 mmol) and sodium hydride (310 mg, 9 mmol) in dry tetrahydrofuran was added a solution of 3-(4-chloro-1,2,5-thiadiazol-3-yl)pyridine (590 mg, 3 mmol) in dry tetrahydrofuran. The reaction mixture was stirred at room temperature for 1 h. Water was added and the mixture was extracted with ether. The ether phase was dried and evaporated to give the title compound. the mixture was extracted with ether The ether phase was dried evaporated