tert-Butanol → (S)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol

Participants

Role	Name	HCID	Charge
Reactant	tert-Butanol	HCID 6386	—
Reactant	Sodium Sulfite	HCID 24437	—
Reactant	1-((1R)-((2R,4R,5S)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)-4-((1R)-((2R,4S,5R)-5-ethylquinuclidin-2-yl)(6-methoxyquinolin-4-yl)methoxy)phthalazine	HCID 51003674	—
Reactant	1-Chloro-3-methyl-2-vinylnaphthalene	HCID 67126076	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	(S)-1-(1-chloro-3-methylnaphthalen-2-yl)ethane-1,2-diol	HCID 67127139	—

Reaction Conditions

Temperature	0 °C

Reaction Steps

A biphasic mixture of AD-mix-α (6.907 g) in tert-butanol (24.5 mL)/H2O (24.5 mL) was cooled to 0° C. and 1-chloro-3-methyl-2-vinylnaphthalene (4D) (1.00 g, 4.93 mmol) was added. The reaction mixture was stirred for 8 h at 0° C. Sodium sulfite (7.4 g) was added at 0° C. and the reaction was stirred for 40 minutes to give a white mixture. The mixture was diluted with dichloromethane and H2O. The mixture was extracted with dichloromethane (3×) and the combined organic layer was dried (MgSO4), filtered, concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give 4E as a white solid (0.920 g).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09102614B2
Source dataset	uspto-grants-2015_08
ORD ID	ord-665a6e6d5e65426a888ecdcb8f824c2e
Source note	uspto-grants-2015_08