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 66.21C (0.300 g, 0.814 mmol) in THF (0.0587 g, 0.814 mmol) at 0° C. was added LAH in THF (1.63 mL, 1.63 mmol, 1.0M). The reaction was stirred for 4.5 hours and then 1N NaOH(aq) was added to quench the mixture. The reaction was extracted three times with EtOAc. After drying over anhydrous magnesium sulfate and filtering, the organic solvent was removed under reduced pressure and the product was then purified on silica gel (0-20% EtOAc in hexanes) to yield 66.21D as a colorless oil (0.250 g, 90.2% yield).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08030354B2
Source dataset	uspto-grants-2011_10
ORD ID	ord-9c8075a28df34b2d9fd93c22c187dc5d
Source note	uspto-grants-2011_10