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

HRID 1859292Notes

Reaction equation

HRID 1859292 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:48]=[CH:47][C:30]2[C:31](=[O:46])[C:32]([C:36]3[CH:41]=[CH:40][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:38][CH:37]=3)([CH3:35])[CH2:33][O:34][C:29]=2[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:46])[C:30]2[CH:47]=[CH:48][C:27]([O:26][CH2:25][O:24][CH3:23])=[CH:28][C:29]=2[O:34][CH2:33][C:32]1([C:36]1[CH:37]=[CH:38][C:39]([O:42][CH2:43][O:44][CH3:45])=[CH:40][CH:41]=1)[CH3:35])([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 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

9-(t-Butyldimethylsilyloxy)-non-1-yne (0.46 g, 1.8 mmol) was dissolved in dry tetrahydrofuran (8 ml) under argon atmosphere and then cooled to -78° C. 2.5M n-Butyllithium (n-BuLi) (0.7 ml, 1.68 mmol) was slowly added dropwise thereto and then the mixture was stirred for 30 minutes. To the mixture was added dropwise 7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran-4-one (200 mg, 6.6 mmol) dissolved in dry tetrahydrofuran (4 ml), and then the reaction mixture was slowly warmed to room temperature. The reaction solution was quenched with water and then extracted with ethyl acetate. The organic layer was separated, dried over magnesium sulfate and concentrated. The residue was subjected to column chromatography (n-hexane:ethyl acetate=4:1) to obtain 350 mg (yield: >100%) of the title compound as a colorless oil.

Workup

  1. temperaturethe reaction mixture was slowly warmed to room temperature
  2. customThe reaction solution was quenched with water
  3. extractionextracted with ethyl acetate
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-90f9d9fb21d34202b0f54bb52b27175b
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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