(But-3-yn-1-yloxy)(tert-butyl)dimethylsilane → 4-[4-(t-Butyl dimethylsilyloxy)-1-butynyl]4-hydroxy-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchroman

HRID 1792361Notes

Reaction equation

HRID 1792361 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][C:11]#[CH:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].C([Li])CCC.[CH3:18][O:19][CH2:20][O:21][C:22]1[CH:31]=[C:30]2[C:25]([C:26](=[O:43])[C:27]([C:33]3[CH:38]=[CH:37][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:35][CH:34]=3)([CH3:32])[CH2:28][O:29]2)=[CH:24][CH:23]=1>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][C:11]#[C:12][C:26]1([OH:43])[C:25]2[C:30](=[CH:31][C:22]([O:21][CH2:20][O:19][CH3:18])=[CH:23][CH:24]=2)[O:29][CH2:28][C:27]1([C:33]1[CH:34]=[CH:35][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:37][CH:38]=1)[CH3:32])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 4304567(But-3-yn-1-yloxy)(tert-butyl)dimethylsilaneHCID 154817637-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-oneHCID 178418339Butyllithium

Product 1

HCID 220334204-[4-(t-Butyl dimethylsilyloxy)-1-butynyl]4-hydroxy-7-methoxymethoxy-3-(4-(methoxymethoxy)phenyl)-3-methylchromanYield 93%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

4-(t-Butyldimethylsilyloxy)-1-butyne (1.17 g, 6.4 mmol) was dissolved in dry tetrahydrofuran (20 ml) under argon atmosphere, which was then cooled down to −78° C. n-Butyllithium (2.29 ml, 5.72 mmol, 2.5M solution in tetrahydrofuran) was slowly added dropwise thereto, and the mixture was stirred at −78° C. for 30 minutes. To this mixture was added dropwise 7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman-4-one (1.14 g, 3.18 mmol) dissolved in dry tetrahydrofuran (10 ml) at −78° C., and the resulting reaction mixture was stirred at room temperature for 3 hours, and the reaction mixture was cooled to 0° C. 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=5:1) to give the title compound (1.6 g, yield 93%) as a colorless oil.

Workup

  1. additionwas slowly added dropwise
  2. customthe resulting reaction mixture
  3. stirringwas stirred at room temperature for 3 hours
  4. temperaturethe reaction mixture was cooled to 0° C
  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-dc2517359cb34385bb9b5302035fc2bd
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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