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Reference Company/Organization
Chiral Magnesium(II) Binaphtholates as Cooper ative Bronste Graduate School of Engineering, CREST
d/Lewis Acid-Base Catalysts for the Highly Enantios elective Nagoya University, Japan Science and Technology Agency (JST)
Addition of Phosphorus Nucleophiles to α, β-Unsaturated Esters
and Ketones Furo-cho, Nagoya 464-8603
Japan
By: Hatano, Manabu; Horibe, Takahiro; Ishihara, Kazuaki

Angewandte Chemie, International Edition (2013), 52(17), 4549-

4553.

10.1002/anie.201300938
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Step 1

Alternative Steps (0)

CAS Reaction Number: 31-614-CAS-27604472

Stage Reagents Catalysts Solvents Conditions

1 Magnesium Iodine - 3 h, rt

2 - - Tetrahydrofuran rt

3 - - - 15 min, 0 °C; 2 h

4 Hydrochloric acid - Water 15 min, 0 °C

Notes
literature preparation

Experimental Protocols

Synthetic Methods

Products Di-2-naphthalenylphosphine oxide

Reactants 2-Bromonaphthalene

Diethyl phosphite

Reagents Magnesium

Hydrochloric acid

Catalysts Iodine

Solvents Tetrahydrofuran

Water

Procedure 1. Stir the mixture of magnesium turnings (480 mg, 20 mmol) and iodine (ca. 3 mg) at room temperature for
3 hours under nitrogen atmosphere.
2. Add THF (10 mL) to the mixture.
3. Add aryl bromide (20 mmol) slowly to the mixture.
4. After exothermic reaction completed, add diethyl phosphite (6.6 mmol) over 15 minutes at 0 °C.
5. After 2 hours, pour 1M HCl (15 mL) to the mixture at 0 °C.
6. Stir the mixture for 15 minutes.
7. Filter the mixture through a Celite pad.
8. Extract the filtrate with chloroform (10 mL × 3).
9. Wash the filtrate with brine (10 mL).
10. Dry the filtrate over Na 2SO 4.
11. Concentrate the organic phase under reduced pressure.
12. Purify the crude product by silica gel column chromatography (eluent; hexane:EtOAc = 3:1 to 1:1).

Scale milligram

CAS Method Number 3-614-CAS-2744283

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