7-phenylheptan-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:; See reaction.notes.procedure_details.

Procedure: To a solution of 7-phenyl-1-heptanol (29.1 g, 151.3 mmol) in 800 mL CH2Cl2 at room temperature was added CBr4 (60.2 g, 181.6 mmol) then triphenylphosphine (47.6 g, 181.6 mmol). After 30 s, the reaction had turned a light green color. TLC indicated that the reaction was complete at this point. The solvent was removed in vacuo to give a greenish-white semisolid. To this material was added 10% EtOAc:90% Hexanes and the resulting suspension was filtered through a pad of silica gel washing well with the same solvent system. There yielded 57 g of a colorless oil as the desired bromide and triphenylphosphine oxide. This oil was then flash chromatographed (Hexanes) to yield 38.6 g, 100% of the bromide as a colorless oil. 1H NMR (CDCl3) δ1.30-1.49 (m, 6H); 1.60 (quintet, J=8.18 Hz, 2H); 2.60 (t, J=8.18 Hz, 2H); 3.39 (t, J=8.18 Hz, 2H); 7.13-7.20 (m, 3H); 7.21-7.31 (m, 2H). The solvent was removed in vacuo to give a greenish-white semisolid 90% Hexanes and the resulting suspension was filtered through a pad of silica gel washing well with the same solvent system

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

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

Procedure: Under nitrogen atmosphere, at 0° C., to a stirring mixture of LiAlH4 (0.51 g, 13.57 mmol) in dry Et2O (35 mL), 7-phenylheptanoic acid (0.7 g, 3.39 mmol) in dry Et2O (5 mL) was dropwise added. The mixture was left to react at rt for 4 h, then at 0° C. H2O (0.51 mL), 3M KOH solution (0.51 mL) and H2O (1.70 mL) were very slowly added. The mixture was stirred for 1 h at 0° C., filtered to remove the solid residue, and the organic phase dried over Na2SO4. The organic solution was again filtered and concentrated to dryness affording the title compound (0.586 g, 90%) as a colorless oil. 1H NMR (CDCl3): δ 1.17-1.27 (m, 1H), 1.34-1.43 (m, 6H), 1.53-1.71 (m, 4H), 2.59-2.67 (m, 2H), 3.66 (t, J=6.5 Hz, 2H), 7.16-7.23 (m, 3H), 7.26-7.34 (m, 2H). was dropwise added The mixture was left to react at rt for 4 h at 0° C filtered to remove the solid residue the organic phase dried over Na2SO4 The organic solution was again filtered concentrated to dryness

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

Procedure: A solution of 7-phenylheptan-1-ol (5 g) in CH2Cl2 (25 mL) was added to a suspension of 1,1,1-tris(acetyloxy)1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane) in CH2Cl2 (25 mL) dropwise with ice-bath cooling. The cooling bath was removed after addition was complete and the resulting mixture was stirred at room temperature for 3 h. After addition of a solution of Na2S2O3 (44 g) in saturated NaHCO3, (35 mL), the resulting mixture was stirred for 45 min and the layers were separated. The aqueous layer was extracted twice with CH2Cl2, and the combined organic phases were washed with water, dried over Na2SO4 and concentrated to yield 7-phenylheptanal as an oil, which was used in the next step without further purification. cooling The cooling bath was removed after addition After addition of a solution of Na2S2O3 (44 g) in saturated NaHCO3, (35 mL) the resulting mixture was stirred for 45 min the layers were separated The aqueous layer was extracted twice with CH2Cl2 the combined organic phases were washed with water dried over Na2SO4 concentrated

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

Procedure: A solution of 7-phenylheptan-1-ol (5 g) in CH2Cl2 (25 mL) was added to a suspension of 1,1,1-tris(acetyloxy)1,1-dihydro-1,2-benziodoxol-3-(1H)-one (Dess-Martin periodinane) in CH2Cl2 (25 mL) dropwise with ice-bath cooling. The cooling bath was removed after addition was complete and the resulting mixture was stirred at room temperature for 3 h. After addition of a solution of Na2S2O3 (44 g) in saturated NaHCO3, (35 mL), the resulting mixture was stirred for 45 min and the layers were separated. The aqueous layer was extracted twice with CH2Cl2, and the combined organic phases were washed with water, dried over Na2SO4 and concentrated to yield 7-phenylheptanal as an oil, which was used in the next step without further purification. cooling The cooling bath was removed after addition After addition of a solution of Na2S2O3 (44 g) in saturated NaHCO3, (35 mL) the resulting mixture was stirred for 45 min the layers were separated The aqueous layer was extracted twice with CH2Cl2 the combined organic phases were washed with water dried over Na2SO4 concentrated

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

Procedure: To a solution of 7-phenyl-1-heptanol (29.1 g, 151.3 mmol) in 800 mL CH2Cl2 at room temperature was added CBr4 (60.2 g, 181.6 mmol) then triphenylphosphine (47.6 g, 181.6 mmol). After 30 s, the reaction had turned a light green color. TLC indicated that the reaction was complete at this point. The solvent was removed in vacuo to give a greenish-white semisolid. To this material was added 10% EtOAc:90% Hexanes and the resulting suspension was filtered through a pad of silica gel washing well with the same solvent system. There yielded 57 g of a colorless oil as the desired bromide and triphenylphosphine oxide. This oil was then flash chromatographed (Hexanes) to yield 38.6 g, 100% of the bromide as a colorless oil. 1H NMR (CDCl3) δ1.30-1.49 (m, 6H); 1.60 (quintet, J=8.18 Hz, 2H); 2.60 (t, J=8.18 Hz, 2H); 3.39 (t, J=8.18 Hz, 2H); 7.13-7.20 (m, 3H); 7.21-7.31 (m, 2H). The solvent was removed in vacuo to give a greenish-white semisolid 90% Hexanes and the resulting suspension was filtered through a pad of silica gel washing well with the same solvent system

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

Procedure: To a solution of 7-phenyl-1-heptanol (29.1 g, 151.3 mmol) in 800 mL CH2Cl2 at room temperature was added CBr4 (60.2 g, 181.6 mmol) then triphenylphosphine (47.6 g, 181.6 mmol). After 30 s, the reaction had turned a light green color. TLC indicated that the reaction was complete at this point. The solvent was removed in vacuo to give a greenish-white semisolid. To this material was added 10% EtOAc:90% Hexanes and the resulting suspension was filtered through a pad of silica gel washing well with the same solvent system. There yielded 57 g of a colorless oil as the desired bromide and triphenylphosphine oxide. This oil was then flash chromatographed (Hexanes) to yield 38.6 g, 100% of the bromide as a colorless oil. 1H NMR (CDCl3) δ1.30-1.49 (m, 6H); 1.60 (quintet, J=8.18 Hz, 2H); 2.60 (t, J=8.18 Hz, 2H); 3.39 (t, J=8.18 Hz, 2H); 7.13-7.20 (m, 3H); 7.21-7.31 (m, 2H). The solvent was removed in vacuo to give a greenish-white semisolid 90% Hexanes and the resulting suspension was filtered through a pad of silica gel washing well with the same solvent system

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

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