tetradecan-2-one

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred, room temperature solution of diisopropylamine (49 mL, 0.35 mol) in dry THF (500 mL) was added a 2.06M solution (170 mL, 0.35 mol) of n-butyl lithium in hexanes in one portion. The solution was cooled to -78° C. To the stirred solution was added neat trimethylsilylchloride (213 mL, 1.68 mol) over 6 minutes. Stirred for 6 minutes. To this solution was added a solution of 2-tetradecanone (71.40 g, 0.3362 mol) in dry THF (710 mL) over 33 minutes. Stirred 5 minutes. To the mixture was added triethylamine (375 mL, 2.7 mol) over 6 minutes followed by a saturated sodium bicarbonate solution (780 mL). The mixture was allowed to warm. When the temperature reached 0° C., petroleum ether (1.7 L) was added, and the organic layer was washed with chilled H2O (2×1.4 L), chilled 0.1M citric acid (3×2 L) and saturated NaCl. The organic layer was dried (Na2SO4) and rotoevaporated and dried in vacuo to give a yellow oil; yield 97.6 g (102%). Stirred 5 minutes to warm reached 0° C. the organic layer was washed with chilled H2O (2×1.4 L) chilled 0.1M citric acid (3×2 L) and saturated NaCl The organic layer was dried (Na2SO4) dried in vacuo to give a yellow oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred, room temperature solution of diisopropylamine (49 mL, 0.35 mol) in dry THF (500 mL) was added a 2.06M solution (170 mL, 0.35 mol) of n-butyl lithium in hexanes in one portion. The solution was cooled to -78° C. To the stirred solution was added neat trimethylsilylchloride (213 mL, 1.68 mol) over 6 minutes. Stirred for 6 minutes. To this solution was added a solution of 2-tetradecanone (71.40 g, 0.3362 mol) in dry THF (710 mL) over 33 minutes. Stirred 5 minutes. To the mixture was added triethylamine (375 mL, 2.7 mol) over 6 minutes followed by a saturated sodium bicarbonate solution (780 mL). The mixture was allowed to warm. When the temperature reached 0° C., petroleum ether (1.7 L) was added, and the organic layer was washed with chilled H2O (2×1.4 L), chilled 0.1M citric acid (3×2 L) and saturated NaCl. The organic layer was dried (Na2SO4) and rotoevaporated and dried in vacuo to give a yellow oil; yield 97.6 g (102%). Stirred 5 minutes to warm reached 0° C. the organic layer was washed with chilled H2O (2×1.4 L) chilled 0.1M citric acid (3×2 L) and saturated NaCl The organic layer was dried (Na2SO4) dried in vacuo to give a yellow oil

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

Procedure: 5-Trimethylsilyl-3-furaldehyde is treated with lithium diisopropylamide and 2-tetradecanone, followed by acetic anhydride to give 3-(1-acetoxy-3-ketopentadecanyl)-5-trimethylsilylfuran. Oxidation by the method described in Example 1 gives 4-(1-acetoxy-3-ketopentadecanyl)-5-hydroxy-2(5H)-furanone.

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

Procedure: 5-Trimethylsilyl-3-furaldehyde is treated with lithium diisopropylamide and 2-tetradecanone, followed by acetic anhydride to give 3-(1-acetoxy-3-ketopentadecanyl)-5-trimethylsilylfuran. Oxidation by the method described in Example 1 gives 4-(1-acetoxy-3-ketopentadecanyl)-5-hydroxy-2(5H)-furanone.

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred, room temperature solution of diisopropylamine (49 mL, 0.35 mol) in dry THF (500 mL) was added a 2.06M solution (170 mL, 0.35 mol) of n-butyl lithium in hexanes in one portion. The solution was cooled to -78° C. To the stirred solution was added neat trimethylsilylchloride (213 mL, 1.68 mol) over 6 minutes. Stirred for 6 minutes. To this solution was added a solution of 2-tetradecanone (71.40 g, 0.3362 mol) in dry THF (710 mL) over 33 minutes. Stirred 5 minutes. To the mixture was added triethylamine (375 mL, 2.7 mol) over 6 minutes followed by a saturated sodium bicarbonate solution (780 mL). The mixture was allowed to warm. When the temperature reached 0° C., petroleum ether (1.7 L) was added, and the organic layer was washed with chilled H2O (2×1.4 L), chilled 0.1M citric acid (3×2 L) and saturated NaCl. The organic layer was dried (Na2SO4) and rotoevaporated and dried in vacuo to give a yellow oil; yield 97.6 g (102%). Stirred 5 minutes to warm reached 0° C. the organic layer was washed with chilled H2O (2×1.4 L) chilled 0.1M citric acid (3×2 L) and saturated NaCl The organic layer was dried (Na2SO4) dried in vacuo to give a yellow oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred, room temperature solution of diisopropylamine (49 mL, 0.35 mol) in dry THF (500 mL) was added a 2.06M solution (170 mL, 0.35 mol) of n-butyl lithium in hexanes in one portion. The solution was cooled to -78° C. To the stirred solution was added neat trimethylsilylchloride (213 mL, 1.68 mol) over 6 minutes. Stirred for 6 minutes. To this solution was added a solution of 2-tetradecanone (71.40 g, 0.3362 mol) in dry THF (710 mL) over 33 minutes. Stirred 5 minutes. To the mixture was added triethylamine (375 mL, 2.7 mol) over 6 minutes followed by a saturated sodium bicarbonate solution (780 mL). The mixture was allowed to warm. When the temperature reached 0° C., petroleum ether (1.7 L) was added, and the organic layer was washed with chilled H2O (2×1.4 L), chilled 0.1M citric acid (3× 2 L) and saturated NaCl. The organic layer was dried (Na2SO4) and rotoevaporated and dried in vacuo to give a yellow oil; yield 97.6 g (102%). Stirred 5 minutes to warm reached 0° C. the organic layer was washed with chilled H2O (2×1.4 L) chilled 0.1M citric acid (3× 2 L) and saturated NaCl The organic layer was dried (Na2SO4) dried in vacuo to give a yellow oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred, room temperature solution of diisopropylamine (49 mL, 0.35 mol) in dry THF (500 mL) was added a 2.06M solution (170 mL, 0.35 mol) of n-butyl lithium in hexanes in one portion. The solution was cooled to -78° C. To the stirred solution was added neat trimethylsilylchloride (213 mL, 1.68 mol) over 6 minutes. Stirred for 6 minutes. To this solution was added a solution of 2-tetradecanone (71.40 g, 0.3362 mol) in dry THF (710 mL) over 33 minutes. Stirred 5 minutes. To the mixture was added triethylamine (375 mL, 2.7 mol) over 6 minutes followed by a saturated sodium bicarbonate solution (780 mL). The mixture was allowed to warm. When the temperature reached 0° C., petroleum ether (1.7 L) was added, and the organic layer was washed with chilled H2O (2×1.4 L), chilled 0.1M citric acid (3× 2 L) and saturated NaCl. The organic layer was dried (Na2SO4) and rotoevaporated and dried in vacuo to give a yellow oil; yield 97.6 g (102%). Stirred 5 minutes to warm reached 0° C. the organic layer was washed with chilled H2O (2×1.4 L) chilled 0.1M citric acid (3× 2 L) and saturated NaCl The organic layer was dried (Na2SO4) dried in vacuo to give a yellow oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred, room temperature solution of diisopropylamine (49 mL, 0.35 mol) in dry THF (500 mL) was added a 2.06M solution (170 mL, 0.35 mol) of n-butyl lithium in hexanes in one portion. The solution was cooled to -78° C. To the stirred solution was added neat trimethylsilylchloride (213 mL, 1.68 mol) over 6 minutes. Stirred for 6 minutes. To this solution was added a solution of 2-tetradecanone (71.40 g, 0.3362 mol) in dry THF (710 mL) over 33 minutes. Stirred 5 minutes. To the mixture was added triethylamine (375 mL, 2.7 mol) over 6 minutes followed by a saturated sodium bicarbonate solution (780 mL). The mixture was allowed to warm. When the temperature reached 0° C., petroleum ether (1.7 L) was added, and the organic layer was washed with chilled H2O (2×1.4 L), chilled 0.1M citric acid (3× 2 L) and saturated NaCl. The organic layer was dried (Na2SO4) and rotoevaporated and dried in vacuo to give a yellow oil; yield 97.6 g (102%). Stirred 5 minutes to warm reached 0° C. the organic layer was washed with chilled H2O (2×1.4 L) chilled 0.1M citric acid (3× 2 L) and saturated NaCl The organic layer was dried (Na2SO4) dried in vacuo to give a yellow oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred, room temperature solution of diisopropylamine (49 mL, 0.35 mol) in dry THF (500 mL) was added a 2.06M solution (170 mL, 0.35 mol) of n-butyl lithium in hexanes in one portion. The solution was cooled to -78° C. To the stirred solution was added neat trimethylsilylchloride (213 mL, 1.68 mol) over 6 minutes. Stirred for 6 minutes. To this solution was added a solution of 2-tetradecanone (71.40 g, 0.3362 mol) in dry THF (710 mL) over 33 minutes. Stirred 5 minutes. To the mixture was added triethylamine (375 mL, 2.7 mol) over 6 minutes followed by a saturated sodium bicarbonate solution (780 mL). The mixture was allowed to warm. When the temperature reached 0° C., petroleum ether (1.7 L) was added, and the organic layer was washed with chilled H2O (2×1.4 L), chilled 0.1M citric acid (3×2 L) and saturated NaCl. The organic layer was dried (Na2SO4) and rotoevaporated and dried in vacuo to give a yellow oil; yield 97.6 g (102%). Stirred 5 minutes to warm reached 0° C. the organic layer was washed with chilled H2O (2×1.4 L) chilled 0.1M citric acid (3×2 L) and saturated NaCl The organic layer was dried (Na2SO4) dried in vacuo to give a yellow oil

Conditions: temp:-78.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred, room temperature solution of diisopropylamine (49 mL, 0.35 mol) in dry THF (500 mL) was added a 2.06M solution (170 mL, 0.35 mol) of n-butyl lithium in hexanes in one portion. The solution was cooled to -78° C. To the stirred solution was added neat trimethylsilylchloride (213 mL, 1.68 mol) over 6 minutes. Stirred for 6 minutes. To this solution was added a solution of 2-tetradecanone (71.40 g, 0.3362 mol) in dry THF (710 mL) over 33 minutes. Stirred 5 minutes. To the mixture was added triethylamine (375 mL, 2.7 mol) over 6 minutes followed by a saturated sodium bicarbonate solution (780 mL). The mixture was allowed to warm. When the temperature reached 0° C., petroleum ether (1.7 L) was added, and the organic layer was washed with chilled H2O (2×1.4 L), chilled 0.1M citric acid (3×2 L) and saturated NaCl. The organic layer was dried (Na2SO4) and rotoevaporated and dried in vacuo to give a yellow oil; yield 97.6 g (102%). Stirred 5 minutes to warm reached 0° C. the organic layer was washed with chilled H2O (2×1.4 L) chilled 0.1M citric acid (3×2 L) and saturated NaCl The organic layer was dried (Na2SO4) dried in vacuo to give a yellow oil

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

Procedure: The title compound was prepared from 2-tetradecanone (5.0 g, 0.023 mol), 2,6-diisopropylphenylisocyanate (4.78 g, 0.023 mol), and lithium diisopropylamide (0.023 mol) using the procedure described in Example 1. Purification by flash chromatography (silica gel, 15% EtOAc/hexane) yielded 4.25 g (0.010 mol, 44%) of the desired product. Purification by flash chromatography (silica gel, 15% EtOAc/hexane)

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

Procedure: 5-Trimethylsilyl-3-furaldehyde is treated with lithium diisopropylamide and 2-tetradecanone, followed by acetic anhydride to give 3-(1-acetoxy-3-ketopentadecanyl)-5-trimethylsilylfuran. Oxidation by the method described in Example 1 gives 4-(1-acetoxy-3-ketopentadecanyl)-5-hydroxy-2(5H)-furanone.