1-Bromoheptadecane

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Heptadecanol (10 g, 39.1 mmol) was placed in a dry 25 ml round bottom flask attached to a reflux condenser and heated to 60° C. under a nitrogen atmosphere. Phosphorous tribromide (10 g, 39.1 mmol) was added dropwise and the resulting solution was stirred for 48 h. The reaction mixture was then cooled in an ice bath and quenched with a saturated solution of NaHCO3 (10 ml). The aqueous layer was extracted with ether (4×10 ml). The combined organic layers were dried over MgSO4, filtered and concentrated. The crude residue was flash chromatographed (hexanes) to afford 7.2 g (57%) of 1-bromoheptadecane as a colorless oil. attached to a reflux condenser The reaction mixture was then cooled in an ice bath quenched with a saturated solution of NaHCO3 (10 ml) The aqueous layer was extracted with ether (4×10 ml) The combined organic layers were dried over MgSO4 filtered concentrated chromatographed (hexanes)

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

Procedure: According to the method of Example 26, from aldehyde 6 (610 mg, 2.28 mmol) and 1-bromoheptadecane (1.82 g, 5.70 mmol), alcohol 62 was obtained as a colorless oil (620 mg, 54% yield).

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

Procedure: According to the method of Example 26, from aldehyde 6 (610 mg, 2.28 mmol) and 1-bromoheptadecane (1.82 g, 5.70 mmol), alcohol 62 was obtained as a colorless oil (620 mg, 54% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (410 mg, 1.62 mmol) and 1-bromoheptadecane (2.07 g, 6.47 mmol), alcohol 44 was obtained as a colorless oil (427 mg, 53% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (410 mg, 1.62 mmol) and 1-bromoheptadecane (2.07 g, 6.47 mmol), alcohol 44 was obtained as a colorless oil (427 mg, 53% yield).

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

Procedure: 2-Methylglycerol (10.6 g) and 10.7 g of 1-bromoheptadecane were reacted and worked up in accordance with Example 5-(i) to give 5.2 g of the above-identified alcohol compound.

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

Procedure: 2-Methylglycerol (10.6 g) and 10.7 g of 1-bromoheptadecane were reacted and worked up in accordance with Example 5-(i) to give 5.2 g of the above-identified alcohol compound.

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Heptadecanol (10 g, 39.1 mmol) was placed in a dry 25 ml round bottom flask attached to a reflux condenser and heated to 60° C. under a nitrogen atmosphere. Phosphorous tribromide (10 g, 39.1 mmol) was added dropwise and the resulting solution was stirred for 48 h. The reaction mixture was then cooled in an ice bath and quenched with a saturated solution of NaHCO3 (10 ml). The aqueous layer was extracted with ether (4×10 ml). The combined organic layers were dried over MgSO4, filtered and concentrated. The crude residue was flash chromatographed (hexanes) to afford 7.2 g (57%) of 1-bromoheptadecane as a colorless oil. attached to a reflux condenser The reaction mixture was then cooled in an ice bath quenched with a saturated solution of NaHCO3 (10 ml) The aqueous layer was extracted with ether (4×10 ml) The combined organic layers were dried over MgSO4 filtered concentrated chromatographed (hexanes)

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 1-Heptadecanol (10 g, 39.1 mmol) was placed in a dry 25 ml round bottom flask attached to a reflux condenser and heated to 60° C. under a nitrogen atmosphere. Phosphorous tribromide (10 g, 39.1 mmol) was added dropwise and the resulting solution was stirred for 48 h. The reaction mixture was then cooled in an ice bath and quenched with a saturated solution of NaHCO3 (10 ml). The aqueous layer was extracted with ether (4×10 ml). The combined organic layers were dried over MgSO4, filtered and concentrated. The crude residue was flash chromatographed (hexanes) to afford 7.2 g (57%) of 1-bromoheptadecane as a colorless oil. attached to a reflux condenser The reaction mixture was then cooled in an ice bath quenched with a saturated solution of NaHCO3 (10 ml) The aqueous layer was extracted with ether (4×10 ml) The combined organic layers were dried over MgSO4 filtered concentrated chromatographed (hexanes)

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

Procedure: According to the method of Example 26, from aldehyde 6 (610 mg, 2.28 mmol) and 1-bromoheptadecane (1.82 g, 5.70 mmol), alcohol 62 was obtained as a colorless oil (620 mg, 54% yield).

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

Procedure: According to the method of Example 26, from aldehyde 4 (410 mg, 1.62 mmol) and 1-bromoheptadecane (2.07 g, 6.47 mmol), alcohol 44 was obtained as a colorless oil (427 mg, 53% yield).

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

Procedure: 2-Methylglycerol (10.6 g) and 10.7 g of 1-bromoheptadecane were reacted and worked up in accordance with Example 5-(i) to give 5.2 g of the above-identified alcohol compound.