Methyl iodide → HCID 59540962, Verbindung

Temperatur

50 °C

To a solution of LDA (made by dropwise addition of nBuLi (2.38M, 13.45 ml, 32.01 mmol) to a −78° C. solution of diisopropyl amine (4.5 ml, 32.0 mmol), in THF (160 ml), in THF, at −78° C.), was added 4-benzyloxy-cyclohexanecarboxylic acid (3.75 g, 16.0 mmol) (Eur. Pat. Appl. (1984), 33 pp. EP 123238A2) dissolved in THF (24 ml). After complete addition, the reaction mixture was stirred at 50° C. for approximately 2 hours. The reaction mixture was cooled to room temperature and MeI (filtered through basic alumina) was added to the reaction mixture, dropwise. After stirring at room temperature for overnight, the reaction mixture was quenched with ice water containing ether, and the aqueous layers were collected. The organic layer was washed one time with water, and the aqueous layer was combined with previous aq. layers. The combined aqueous layers were acidified with 2N HCl (pH=1), and extracted four times with ether. The ether extracts were brined, dried over MgSO4, filtered, and concentrated giving 3.3 g (83%) of 4-benzyloxy-1-methyl-cyclohexanecarboxylic acid as an off white solid. M−H=247.

1. additionAfter complete addition
2. temperatureThe reaction mixture was cooled to room temperature
3. stirringAfter stirring at room temperature for overnight
4. customthe reaction mixture was quenched with ice water
5. additioncontaining ether
6. customthe aqueous layers were collected
7. washThe organic layer was washed one time with water
8. extractionextracted four times with ether
9. dry with materialdried over MgSO4
10. filtrationfiltered
11. concentrationconcentrated

ORD-Eintrag

ord-4bb1cc1386474c8087733c07196206d7

Quelldatensatz

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08008298B2