Methyl iodide → HCID 18177916, compound

HRID 394929Notes

Reaction equation

HRID 394929 reaction equation
[CH3:1][C:2]1([CH3:19])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([CH:14]([CH3:18])[C:15]([OH:17])=[O:16])[CH:5]=[CH:4][C:3]1=2.[CH:20]([N-]C(C)C)(C)C.[Li+].CI>C1COCC1>[CH3:18][C:14]([C:6]1[CH:5]=[CH:4][C:3]2[C:2]([CH3:19])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]=2[CH:7]=1)([CH3:20])[C:15]([OH:17])=[O:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2724682Lithium diisopropylamideHCID 18177860HCID 18177860, compound

Product 1

HCID 18177916HCID 18177916, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2 g of (RS)-2-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)-propanoic acid dissolved in 100 ml THF were treated with 9.6 ml of a 2M lithium diisopropylamide solution, at −23° C. The mixture was kept at that temperature for 15 min. then, 1.19 ml of methyl iodide were added dropwise. The reaction mixture was kept at 0° C. for 4 hours then allowed to warm at room temperature for several days. The mixture was quenched with 100 ml of 1N hydrochloric acid solution. The mixture was extracted with three portions of 100 ml of ethyl acetate. The combined organic extracts were washed with 100 ml of a saturated aqueous sodium chloride solution. The organic phase was dried with MgSO4, and the solvent was evaporated. The yellow oil was purified by flash chromatography (SiO2, 20% ethyl acetate/hexanes). 1H NMR (CDCl3): 7.31 (d, J=2.2 Hz, 1H), 7.24 (d, J=8.3 Hz, 1H), 7.15 (dd, J=8.3, 2.2 Hz, 1H), 1.67 (s, 4H), 1.58 (s, 6H), 1.27 (s, 6H), 1.26 (s, 6H).

Workup

  1. waitThe reaction mixture was kept at 0° C. for 4 hours
  2. customThe mixture was quenched with 100 ml of 1N hydrochloric acid solution
  3. extractionThe mixture was extracted with three portions of 100 ml of ethyl acetate
  4. washThe combined organic extracts were washed with 100 ml of a saturated aqueous sodium chloride solution
  5. dry with materialThe organic phase was dried with MgSO4
  6. customthe solvent was evaporated
  7. customThe yellow oil was purified by flash chromatography (SiO2, 20% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-413ce734312541e1942c4bae0c9b4e55
Source dataset
uspto-grants-2003_08
Patent number
US06603012B2

Reaction notes

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