Methyl iodide → (+/-)-3-(Cyclopentyloxy)-4-methoxy-alpha-methylbenzeneacetonitrile

A mixture of 3-(cyclopentyloxy)-4-methoxybenzeneacetonitrile (20 g) in THF (200 ml) was stirred at −78° C. under a N2 flow. N-(1-methylethyl)-2-propanamine lithium salt (45 ml) was added dropwise and the resulting mixture was stirred for 30 minutes at −78° C. Iodomethane (13.5 g) was added dropwise and the resulting reaction mixture was allowed to warm to RT. The reaction mixture was stirred for 2 hours. The mixture was quenched with a saturated aqueous NH4Cl solution (200 ml) and was extracted with CH2Cl2(3×100 ml). The separated organic layer was dried (MgSO4), filtered and the solvent was evaporated, yielding 17.7 g (100% ) of (±)-3-(cyclopentyloxy)-4-methoxy-α-methylbenzeneacetonitrile (interm. 8).

1. stirringthe resulting mixture was stirred for 30 minutes at −78° C
2. customthe resulting reaction mixture
3. temperatureto warm to RT
4. stirringThe reaction mixture was stirred for 2 hours
5. customThe mixture was quenched with a saturated aqueous NH4Cl solution (200 ml)
6. extractionwas extracted with CH2Cl2(3×100 ml)
7. dry with materialThe separated organic layer was dried (MgSO4)
8. filtrationfiltered
9. customthe solvent was evaporated

ORDレコード

ord-7f6d93361d4a46b589aced7663c5f304

出典データセット

uspto-grants-2002_06

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US06403805B1