HCID 10899886, compound → 3-(3-Methoxy-3-methylbutyl)-5,5-dimethylcyclohexan-1-one

HRID 483700Notes

Reaction equation

HRID 483700 reaction equation
[CH3:1][Li].[CH3:3][O:4][C:5]([CH3:17])([CH3:16])[CH2:6][CH2:7][CH:8]1[CH2:13][C:12]([CH3:14])=[CH:11][C:10](=[O:15])[CH2:9]1>O1CCCC1.C(OCC)C.[Cu]I>[CH3:3][O:4][C:5]([CH3:17])([CH3:16])[CH2:6][CH2:7][CH:8]1[CH2:13][C:12]([CH3:1])([CH3:14])[CH2:11][C:10](=[O:15])[CH2:9]1

Participants

6

Reactant 2

HCID 10899886HCID 10899886, compoundHCID 178418348HCID 178418348, compound

Product 1

HCID 147939963-(3-Methoxy-3-methylbutyl)-5,5-dimethylcyclohexan-1-one

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of copper(I) iodide (6.0 g, 0.032 mol) in tetrahydrofuran (120 mL) cooled to 0~C. was added a methyllithium solution (45 mL of a 1.4M solution in diethyl ether, 0.063 mol). After stirring 0.5 hour, 3-(3-methoxy-3-methylbutyl)-5-methylcyclohex-5-en-1-one (2.0 g, 0.0095 mL) in tetrahydrofuran (80 mL) was slowly added. After stirring 2.5 hours, the mixture was added to ice cold dilute hydrochloric acid. Subsequent workup yielded 3-(3-methoxy-3-methylbutyl)-5,5-dimethylcyclohexan-1-one, bp0.5 125-130~C. (1.3 g); NMR (CDCl3) δ 0.9(s,3H), 1.1(s,3H), 1.1(s,6H), 1.2-1.6(m,6H), 1.6-2.5(m,5H), 3.2(s,3H); IR(neat) 2960, 1715, 1365, 1085 cm-1. MS(m/e) 41, 55, 73, 138, 161, 211, 212.

Workup

  1. temperaturecooled to 0~C
  2. stirringAfter stirring 2.5 hours
  3. additionthe mixture was added to ice cold dilute hydrochloric acid

Sources & evidence

ORD record
ord-ff918eb5cb6f49e989fd7ef6ba0b2e17
Source dataset
uspto-grants-1993_07
Patent number
US05225608

Reaction notes

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