Tetrahydrofuran → HCID 57705690, compound

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Sodium Hydroxide	HCID 14798	—
Reactant	Aluminium lithium hydride	HCID 21226445	—
Reactant	[1,1′-Biphenyl]-4-carboxylic acid, 2-(6,6-dimethyl-1-cyclohexen-1-yl)-2′-fluoro-5′-methoxy-, methyl ester	HCID 57706936	—
Product	HCID 57705690	HCID 57705690	90.2%

Reaction Steps

To a stirred solution of T12.6 (0.300 g, 0.814 mmol) in THF (0.0587 g, 0.814 mmol) at 0° C. was added LAH (1.63 mL, 1.63 mmol, 1.0M). The resulting mixture was stirred for 4.5 hours. Next, 1N NaOH(aq) was added to quench the mixture. The reaction was extracted three times with EtOAc. The combined organic layers were dried over anhydrous magnesium sulfate and filtered. The organic solvent was removed under reduced pressure, and the product was purified on silica gel (0-20% EtOAc in hexanes) to yield T12.7 as a colorless oil (0.250 g, 90.2% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08748462B2
Source dataset	uspto-grants-2014_06
ORD ID	ord-46f2613607444e85898d59f55596133d
Source note	uspto-grants-2014_06