Methyl iodide → 4-(1,1-Dimethyl-2-butynyl)anisole

HRID 481524Notes

Reaction equation

HRID 481524 reaction equation
[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:7])[CH:3]=[C:4](Br)Br.[Li][CH2:17]CCC.CI>C1COCC1>[CH3:1][C:2]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=1)([CH3:7])[C:3]#[C:4][CH3:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 190664224-(1,1-Dimethyl-3,3-dibromo-2-propenyl)anisoleHCID 178418339Butyllithium

Product 1

HCID 190665084-(1,1-Dimethyl-2-butynyl)anisoleYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of Compound 53 (335 mg, 1.00 mmol) in THF (10 ml) was added n-BuLi (1.69M in hexane, 1.19 ml, 2.01 mmol) at -78° C. under N2, then warmed up to 0° C., and stirred for 1.5 h. MeI (213 mg, 1.50 mmol) was added, and stirred for 1.5 h at 0° C. The mixture was quenched by the addition of NH4Cl aq., and extracted with CH2Cl2. The combined organic layers were dried over MgSO4, filtered, and concentrated. This was purified by SiO2 chromatography to give Compound 54 (162 mg, 86%) as a colorless oil.

Workup

  1. stirringstirred for 1.5 h at 0° C
  2. customThe mixture was quenched by the addition of NH4Cl aq.
  3. extractionextracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThis was purified by SiO2 chromatography

Sources & evidence

ORD record
ord-2ea3746090b5481bb563e3337c69d2d3
Source dataset
uspto-grants-1998_08
Patent number
US05789423

Reaction notes

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