Ammonia → (4-(5-Methyl-furan-2-ylmethyl)-phenyl)-methanol

To a mixture of lithium aluminumhydride (230 mg, 4.9 mmol) and tetrahydrofuran (15 mL) was added aluminum chloride (830 mg, 6.2 mmol) at 0° C., which was stirred for 30 minutes at room temperature. A mixture of 4-(hydroxy-(5-methyl-furan-2-yl)-methyl)-benzaldehyde (320 mg, 1.5 mmol) described in Manufacturing Example 46-1-1 and tetrahydrofuran (5 mL) was added dropwise into the reaction mixture at 0° C., and stirred for 2 hours at that temperature. A 28% aqueous ammonia solution was added dropwise into the reaction mixture at the same temperature to quench the excess reagent. The reaction mixture was cooled to room temperature, and filtered by being passed through a Celite bed. The filtrate was concentrated under a reduced pressure to obtain the title compound (330 mg) as a crude product. This compound was used in the following reaction without further purification.

1. additionwas added dropwise into the reaction mixture at 0° C.
2. stirringstirred for 2 hours at that temperature
3. customto quench the excess reagent
4. temperatureThe reaction mixture was cooled to room temperature
5. filtrationfiltered
6. concentrationThe filtrate was concentrated under a reduced pressure

ORD record

ord-f20aa5a2ea394992b7a5e9ed3eb94a10

Source dataset

uspto-grants-2010_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07691882B2