1,1-Dichloroethane → (Z)-7-[(1R,2S,3R)-3-Hydroxy-5-oxo-2-(1-oxo-indan-5-yl)-cyclopentyl]-hept-5-enoic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	1,1-Dichloroethane	HCID 6365	—
Reactant	2,3-Dichloro-5,6-dicyano-1,4-benzoquinone	HCID 6775	—
Reactant	Sodium Bicarbonate	HCID 516892	—
Reactant	(Z)-7-{(1R,2S,3R)-3-Hydroxy-2-[1-(4-methoxy-benzyloxy)-indan-5-yl]-5-oxo-cyclopentyl}-hept-5-enoic acid methyl ester	HCID 69595718	—
Solvent	Water	HCID 962	—
Solvent	Dichloromethane	HCID 6344	—
Product	(Z)-7-[(1R,2S,3R)-3-Hydroxy-5-oxo-2-(1-oxo-indan-5-yl)-cyclopentyl]-hept-5-enoic acid methyl ester	HCID 11955337	64.3%

Reaction Steps

DDQ (10 mg, 0.041 mmol) was added to a mixture of 15-5 (11 mg, 0.021 mmol) in dichloromethane (0.5 mL)/water (25 μL). After 1 h, dichloroethane (0.5 mL) was added and the reaction was stirred overnight. Saturated NaHCO3 solution was added and the resulting mixture was extracted with dichloromethane (3×20 mL). The combined dichloromethane solution was washed with brine and then was dried (Na2SO4), filtered and evaporated. Purification of the residue by flash chromatography on silica gel (60% ethyl acetate/hexanes) gave 15-8 (5 mg, 59%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07091231B2
Source dataset	uspto-grants-2006_08
ORD ID	ord-aab96c42632a4a4890d68c2d0cb345b0
Source note	uspto-grants-2006_08