9-(t-Butyldimethylsilyloxy)-1-nonyne → 4-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

HRID 1792305Notes

Reaction equation

HRID 1792305 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[CH:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[CH3:23][O:24][CH2:25][O:26][C:27]1[CH:36]=[C:35]2[C:30]([C:31](=[O:48])[C:32]([C:38]3[CH:43]=[CH:42][C:41]([O:44][CH2:45][O:46][CH3:47])=[CH:40][CH:39]=3)([CH3:37])[CH2:33][O:34]2)=[CH:29][CH:28]=1>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:31]1([OH:48])[C:30]2[C:35](=[CH:36][C:27]([O:26][CH2:25][O:24][CH3:23])=[CH:28][CH:29]=2)[O:34][CH2:33][C:32]1([C:38]1[CH:39]=[CH:40][C:41]([O:44][CH2:45][O:46][CH3:47])=[CH:42][CH:43]=1)[CH3:37])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 140273559-(t-Butyldimethylsilyloxy)-1-nonyneHCID 154817637-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-oneHCID 178418339Butyllithium

Product 1

HCID 220330974-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchromanYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

9-(t-Butyl dimethylsilyloxy)-1-nonyne (7.1 g, 27.9 mmol) was dissolved in dry tetrahydrofuran (70 mL) under argon atmosphere, which was then cooled down to −78° C. n-Butyllithium (15.1 ml, 25.1 mmol, 1.66 mol/l solution in tetrahydrofuran) was slowly added dropwise thereto, and the mixture was stirred at −20° C. for 80 minutes. To this mixture was added dropwise 7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-one (2.0 g, 5.58 mmol) dissolved in dry tetrahydrofuran (15 mL) at −20° C., and the resulting reaction mixture was stirred at the same temperature for 3 hours, and then stirred at −10° C. overnight. The reaction was quenched with water, and the reaction solution was extracted with ethyl acetate. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated. The residue was subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=9:1) to give the title compound (3.37 g, yield 99%) as a colorless oil.

Workup

  1. additionwas slowly added dropwise
  2. customthe resulting reaction mixture
  3. stirringwas stirred at the same temperature for 3 hours
  4. stirringstirred at −10° C. overnight
  5. customThe reaction was quenched with water
  6. extractionthe reaction solution was extracted with ethyl acetate
  7. washThe organic layer was washed with water and saturated sodium chloride solution
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-434dffa6d95946b5aedc86a980a81a6f
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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