2-phenylmethoxyacetaldehyde

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:

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

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

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

Procedure: 2-(Benzyloxy)acetaldehyde (5 g, 33.3 mmol) in dry THF (10 mL) was added dropwise to a stirred and cooled solution of allylmagnesium chloride (25 mL, 2 M in THF, 50 mmol) in THF (100 mL) at −78° C. After the addition, the solution was allowed to warm to 0° C. and quenched with saturated NH4Cl solution. After standard aqueous work up, the residue was purified over silica using EtOAc and hexane to give 1-(benzyloxy)pent-4-en-2-ol (11). After the addition quenched with saturated NH4Cl solution After standard aqueous work up, the residue was purified over silica

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

Procedure: Magnesium metal (5 g., 0.206 mole) is suspended in tetrahydrofuran (100 ml.) in a three-necked, round-bottomed flask protected by a dry ice condenser and equipped with a mechanical stirrer. The stirrer is started and vinyl bromide (22 g., 0.206 mole) in tetrahydrofuran is added at such a rate as to keep the solvent refluxing. The reaction mixture is refluxed for 0.5 hours after the addition is complete. The reaction mixture is then cooled to 0°-5° C. and benzyloxyacetaldehyde (24 g., 0.16 mole) in tetrahydrofuran (15 ml.) is added dropwise. After 1.5 hours at 0°-5° C., there is added acetic anhydride (26 g., 0.255 mole) and the reaction mixture is allowed to come to room temperature. After 20 hours at room temperature, ice water (500 ml.) is added and the product is extracted into ethyl acetate (3 × 100 ml.). The ethyl acetate extract is washed with brine, dried (Na2SO4), and distilled. There is obtained 17 g. (49%) of the title compound, b.p. 85°-95° C./0.05 mm. protected by a dry ice condenser equipped with a mechanical stirrer refluxing The reaction mixture is refluxed for 0.5 hours after the addition The reaction mixture is then cooled to 0°-5° C. to come to room temperature After 20 hours at room temperature the product is extracted into ethyl acetate (3 × 100 ml.) The ethyl acetate extract is washed with brine dried (Na2SO4) distilled There is obtained 17 g

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