Dimethylformamide → 3,3,7-Trimethyl-2,3-dihydro-1-benzofuran-5-carbaldehyde

Temperature

-78 °C

To a nitrogen flushed 50 mL round bottom flask were added 5-bromo-3,3,7-trimethyl-2,3-dihydro-1-benzofuran (0.11 g, 0.46 mmol) and THF (3 mL). A solution of n-BuLi (0.20 mL, 2.5 M solution in hexanes) was added via a syringe at −78° C. The reaction mixture was stirred at −78° C. for 10 minutes, then DMF (0.053 mL, 0.68 mmol) was added. The reaction mixture was allowed to warm to room temperature. EtOAc (20 mL) and wet silica gel (5 g silica gel/0.5 mL of water) were added. The resulting mixture was stirred at room temperature for 10 minutes and then filtered. The resulting solid was rinsed with EtOAc. The filtrate was concentrated. The residue was purified on a silica gel column eluting with a gradient of 100% hexanes to 10% EtOAc/hexanes to give the title intermediate (40 mg) as colorless solid.

1. customTo a nitrogen flushed 50 mL round bottom flask
2. temperatureto warm to room temperature
3. stirringThe resulting mixture was stirred at room temperature for 10 minutes
4. filtrationfiltered
5. washThe resulting solid was rinsed with EtOAc
6. concentrationThe filtrate was concentrated
7. customThe residue was purified on a silica gel column
8. washeluting with a gradient of 100% hexanes to 10% EtOAc/hexanes

ORD record

ord-d468c769fc624618bddcfaf4d05e458c

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08742110B2