1-phenyl-3-trimethylsilylprop-2-yn-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:; See reaction.notes.procedure_details.

Procedure: Place a mixture of α-[(trimethylsilyl)ethynyl]-benzenemethanol (1.87 g, 9.13 mmol) and tetrahydrofuran (11 mL) under argon atmosphere. Add, by dropwise addition, tetra-n-butylammonium fluoride (11 mL of a 1M solution in tetrahydrofuran, 11 mmol). Stir for 1 hour at room temperature and partition between ethyl ether and water. Separate the organic phase, wash with saturated aqueous sodium chloride, dry (MgSO4), filter, and concentrate in vacuo to yield the title compound. partition between ethyl ether and water Separate the organic phase wash with saturated aqueous sodium chloride dry (MgSO4) filter concentrate in vacuo

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

Procedure: Place lithium hexamethyldisilazane (12 mL of a IM solution in tetrahydrofuran, 12 mmol) under an argon atmosphere and cool to 0° C. Add trimethylsilylacetylene (1.7 mL, 12 mmol) and stir for 1 hour at 0° C. Add benzaldehyde (1.06 g, 10 mmol) in tetrahydrofuran (25 mL). Allow to warm to room temperature and stir for 3 hours. Pour the mixture into ethyl ether and water, separate the organic phase and evaporate the solvent in vacuo. Filter the oil through silica gel (20% ethyl acetate/hexane) and evaporate the solvent in vacuo to yield the title compound. separate the organic phase evaporate the solvent in vacuo Filter the oil through silica gel (20% ethyl acetate/hexane) evaporate the solvent in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Place a mixture of α-[(trimethylsilyl)ethynyl]-benzenemethanol (4.09 g, 20 mmol) and tetrahydrofuran (25 mL) under argon atmosphere and cool to 0° C. Add, by dropwise addition, tetra-n-butylammonium fluoride (25 mL of a 1M solution in tetrahydrofuran, 25 mmol). Allow to warm to room temperature and stir for 1 hour. Partition between ethyl ether and water. Separate the organic phase, wash with saturated aqueous sodium chloride and concentrate in vacuo. Purify by silica gel chromatography (15% ethyl acetate/hexane) then purify further by distillation to yield 2.15 g of the title compound; bp 100°-110° C. @ 0.1 mm Hg. Allow to warm to room temperature Partition between ethyl ether and water Separate the organic phase wash with saturated aqueous sodium chloride concentrate in vacuo Purify by silica gel chromatography (15% ethyl acetate/hexane) then purify further by distillation

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Place lithium hexamethyldisilazane (20 mL of a 1M solution in tetrahydrofuran, 20 mmol) under an argon atmosphere and cool to 0° C. Add, by dropwise addition, trimethylsilylacetylene (2.83 mL, 20 mmol) and stir for 1 hour at 0° C. Add benzaldehyde (2.03 mL, 20 mmol) in tetrahydrofuran (10 mL). Allow to warm to room temperature and stir for 1 hour. Pour the mixture into ethyl ether and water, separate the organic phase and evaporate the solvent in vacuo. Filter the oil through silica gel (20% ethyl acetate/hexane) and evaporate the solvent in vacuo to yield 4.09 g of the title compound. Allow to warm to room temperature stir for 1 hour separate the organic phase evaporate the solvent in vacuo Filter the oil through silica gel (20% ethyl acetate/hexane) evaporate the solvent in vacuo

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

Procedure: In step a, trimethylsilylacetylene (1) can first be reacted with a non-nucleophilic base, such as lithium hexamethyldisilazane, in a suitable aprotic solvent, such as tetrahydrofuran. The resulting lithium acetylide can then be reacted with the appropriate benzaldehyde compound of structure 2 to give the corresponding α-[(trimethylsilyl)ethynyl]-benzenemethanol compound of structure 3.

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

Procedure: Place a mixture of α-[(trimethylsilyl)ethynyl]-benzene-methanol (1.87 g, 9.13mmol) and tetrahydrofuran (11 mL) under argon atmosphere. Add, by dropwise addition, tetra-n-butylammonium fluoride (11 mL of a 1M solution in tetrahydrofuran, 11 mmol). Stir for 1 hour at room temperature and partition between ethyl ether and water. Separate the organic phase, wash with saturated aqueous sodium chloride, dry (MgSO4), filter, and concentrate in vacuo to yield the title compound. partition between ethyl ether and water Separate the organic phase wash with saturated aqueous sodium chloride dry (MgSO4) filter concentrate in vacuo

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

Procedure: Place lithium hexamethyldisilazane (12 mL of a IM solution in tetrahydrofuran, 12 mmol) under an argon atmosphere and cool to 0° C. Add trimethylsilylacetylene (1.7 mL, 12 mmol) and stir for 1 hour at 0° C. Add benzaldehyde (1.06 g, 10 mmol) in tetrahydrofuran (25 mL). Allow to warm to room temperature and stir for 3 hours. Pour the mixture into ethyl ether and water, separate the organic phase and evaporate the solvent in vacuo. Filter the oil through silica gel (20% ethyl acetate/hexane) and evaporate the solvent in vacuo to yield the title compound. separate the organic phase evaporate the solvent in vacuo Filter the oil through silica gel (20% ethyl acetate/hexane) evaporate the solvent in vacuo

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Place a mixture of α-[(trimethylsilyl)ethynyl]-benzene-methanol (4.09 g, 20 mmol) and tetrahydrofuran (25 mL) under argon atmosphere and cool to 0° C. Add, by dropwise addition, tetra-n-butylammonium fluoride (25 mL of a 1M solution in tetrahydrofuran, 25 mmol). Allow to warm to room temperature and stir for 1 hour. Partition between ethyl ether and water. Separate the organic phase, wash with saturated aqueous sodium chloride and concentrate in vacuo. Purify by silica gel chromatography (15% ethyl acetate/hexane) then purify further by distillation to yield 2.15 g of the title compound; bp 100°-110° C. @0.1 mm Hg. Allow to warm to room temperature Partition between ethyl ether and water Separate the organic phase wash with saturated aqueous sodium chloride concentrate in vacuo Purify by silica gel chromatography (15% ethyl acetate/hexane) then purify further by distillation