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

HRID 1604426Notes

Reaction equation

[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH2:15][C:16]#[N:17])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Li].[CH3:19]C(NC(C)C)C.IC>C1COCC1>[CH:1]1([O:6][C:7]2[CH:8]=[C:9]([CH:15]([CH3:19])[C:16]#[N:17])[CH:10]=[CH:11][C:12]=2[O:13][CH3:14])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

Conditions

Temperature: -78 °C

Procedure

A mixture of 3-(cylcopentyloxy)-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×φml). 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).

Workup

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

Sources & evidence

ORD record: ord-8b78e3eed0174b4fa02bacb28dbd6090
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05994376

Reaction notes

Loading…