dec-2-en-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:

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

Procedure: Phenol 34 (486 mg, 3.2 mmol), 2-decenol 26 g (500 mg, 3.2 mmol), TPP (965 mg, 3.68 mmol), and DEAD (641 mg, 3.68 mmol) in 32 ml ether were reacted according to the procedure for compound 35a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5-90/10 (v/v, Hex/EtOAc). Evaporation of solvent yielded 603 mg (65%) of colorless needles. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5-90/10 (v/v, Hex/EtOAc) Evaporation of solvent

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

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

Procedure: Phenol 34 (486 mg, 3.2 mmol), 2-decenol 26 g (500 mg, 3.2 mmol), TPP (965 mg, 3.68 mmol), and DEAD (641 mg, 3.68 mmol) in 32 ml ether were reacted according to the procedure for compound 35a. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5-90/10 (v/v, Hex/EtOAc). Evaporation of solvent yielded 603 mg (65%) of colorless needles. The crude product was purified via flash chromatography over silica gel with gradual elutions from 95/5-90/10 (v/v, Hex/EtOAc) Evaporation of solvent

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: A suspension of 19 g of zinc dust and 29 g of cuprous chloride powder in 125 ml of ether are stirred under reflux for thirty minutes. Diiodomethane (14.8 ml) is added dropwise over a twenty minute period. No external heat is required and the addition is carried out at a rate sufficient to maintain reflux (36°-41° C). 1.5 g of the product produced in Example VI, 9,10,10-trimethyl-tricyclo-(4.3.1.04,9)-dec-2-en-1-ol, is then added dropwise over a twenty minute period without external heating. Reflux is maintained (41°-46° C) throughout addition of the dec-2-en-1-ol. The reaction mass is refluxed daily for 8.5 hours for 5 days (42 hours in all) adding more ether and diiodomethane as required. The course of the reaction is followed by GLC (20 feet × 1/4 inch 5% SE-30 prog. 100°-220° C at [4°/min.). under reflux for thirty minutes No external heat the addition to maintain reflux (36°-41° C) Reflux is maintained (41°-46° C) The reaction mass is refluxed daily for 8.5 hours for 5 days (42 hours in all) 100°-220° C