Potassium tert-butoxide → 2-Methoxy-1-(3-methylbutyl)-1-vinyl-1,4-dihydronaphthalene

HRID 494666Notes

Reaction equation

HRID 494666 reaction equation
[CH3:1]C(C)([O-])C.[K+].[CH3:7][O:8][C:9]1[C:10]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])([CH:19]=O)[C:11]2[C:16]([CH2:17][CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH3:7][O:8][C:9]1[C:10]([CH2:21][CH2:22][CH:23]([CH3:25])[CH3:24])([CH:19]=[CH2:1])[C:11]2[C:16]([CH2:17][CH:18]=1)=[CH:15][CH:14]=[CH:13][CH:12]=2

Participants

5

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 876087112-Methoxy-1-(3-methylbutyl)-1,4-dihydronaphthalene-1-carbaldehyde

Product 1

HCID 688756232-Methoxy-1-(3-methylbutyl)-1-vinyl-1,4-dihydronaphthaleneYield 87%

Reagents, catalysts & solvents 2

HCID 74505Methyltriphenyliphosphonium bromideCatalystHCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of methyltriphenylphosphonium bromide (0.62 g, 1.7 mmol) in tetrahydrofuran (3 mL) at 0° C. was added a solution of 1.0 M potassium t-butoxide in tetrahydrofuran (1.5 mL, 1.5 mmol). The mixture was allowed to warm to room temperature and stirred for 1 h. After which, the solution was cooled to 40° C. and a solution of Example 181A (0.15 g, 0.6 mmol) in tetrahydrofuran (3 mL) was added dropwise. The reaction mixture was stirred at −40° C. for 1 h, and then allowed to warm to room temperature and stirred for 2 h. The solution was quenched with saturated NH4Cl solution (15 mL) and extracted with ethyl acetate (3× 10 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated in vacuo. Column chromatography on silica (hexane) afforded product as a colorless oil (0.13 g, 87%). 1H NMR (300 MHz, CDCl3) δ ppm 0.63 (m, 1H), 0.77 (dd, J=12.87, 6.62 Hz, 6H), 0.90 (m, 1H), 1.40 (m, 1H), 1.79 (m, 1H), 2.17 (m, 1H), 3.50 (d, J=3.68 Hz, 2H), 3.59 (s, 3H), 4.99 (m, 3H), 6.00 (dd, J=17.65, 10.66 Hz, 1H), 7.16 (m, 4H).

Workup

  1. temperatureAfter which, the solution was cooled to 40° C.
  2. stirringThe reaction mixture was stirred at −40° C. for 1 h
  3. temperatureto warm to room temperature
  4. stirringstirred for 2 h
  5. customThe solution was quenched with saturated NH4Cl solution (15 mL)
  6. extractionextracted with ethyl acetate (3× 10 mL)
  7. dry with materialThe combined organic extracts were dried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a431833a513d4067892bb0072e02a806
Source dataset
uspto-grants-2009_05
Patent number
US07538105B2

Reaction notes

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