Water → HCID 18770243, compound

HRID 1792387Notes

Reaction equation

HRID 1792387 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[CH2:5][O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].C([Li])CCC.[CH3:22][O:23][C:24]1[CH:33]=[C:32]2[C:27]([C:28](=[O:42])[CH:29]([C:34]3[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=3)[CH2:30][S:31]2)=[CH:26][CH:25]=1.O>O1CCCC1>[Si:7]([O:6][CH2:5][C:4]1[CH:3]=[C:2]([C:28]2([OH:42])[C:27]3[C:32](=[CH:33][C:24]([O:23][CH3:22])=[CH:25][CH:26]=3)[S:31][CH2:30][CH:29]2[C:34]2[CH:39]=[CH:38][C:37]([O:40][CH3:41])=[CH:36][CH:35]=2)[CH:16]=[CH:15][CH:14]=1)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 962WaterHCID 111303687-Methoxy-3-(4-methoxyphenyl)thiochroman-4-oneHCID 220331471-Bromo-3-((((1,1-dimethylethyl)dimethylsilyl)oxy)methyl)benzeneHCID 178418339Butyllithium

Product 1

HCID 18770243HCID 18770243, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of (3-bromobenzyloxy)-t-butyldimethylsilane (2.207 g, 7.326 mmol) in dry tetrahydrofuran (20 ml) was added n-butyl lithium (4.18 ml, 6.66 mmol, 1.59M tetrahydrofuran solution) at −78° C. over 25 minutes and stirred for 50 minutes. Then to the reaction mixture was added 7-methoxy-3-(4-methoxyphenyl)thiochroman-4-one (1 g, 3.33 mmol) dissolved in tetrahydrofuran at the same temperature over 10 minutes. The reaction mixture was stirred for 20 minutes at −78° C., followed at −15° C. for 12 h and at 0° C. for 8 h. When the reaction was completed, water was added to the reaction solution which was then extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified with column chromatography (n-hexane:ethyl acetate=8:2) to give 0.49 g (yield: 28%) of the title compound as a colorless oil. In this reaction 0.55 g (55%) of the unreacted starting compound was recovered.

Workup

  1. stirringThe reaction mixture was stirred for 20 minutes at −78° C.
  2. waitfollowed at −15° C. for 12 h and at 0° C. for 8 h
  3. extractionwas then extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified with column chromatography (n-hexane:ethyl acetate=8:2)

Sources & evidence

ORD record
ord-183140d4111443ef90741e80372e6977
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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