Ammonium Chloride → 4-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman

HRID 1859312Notes

Reaction equation

HRID 1859312 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][C:25]1[CH:34]=[C:33]2[C:28]([C:29](=[O:44])[C:30]([C:36]3[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=3)([CH3:35])[CH2:31][S:32]2)=[CH:27][CH:26]=1.[Cl-].[NH4+]>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][C:29]1([OH:44])[C:28]2[C:33](=[CH:34][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[S:32][CH2:31][C:30]1([C:36]1[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=1)[CH3:35])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 109799547-Methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-oneHCID 140273559-(t-Butyldimethylsilyloxy)-1-nonyneHCID 178418339Butyllithium

Product 1

HCID 220331564-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]-4-hydroxy-7-methoxy-3-(4-methoxyphenyl)-3-methylthiochromanYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To 9-(t-butyldimethylsilyloxy)-1-nonyne (2.23 g, 8.75 mmol) was added dry tetrahydrofuran (30 ml). Then n-butyl lithium (4.65 ml, 7.87 mol, 1.69 mol/l tetrahydrofuran solution) was added dropwise thereto at -78° C. and the resulting mixture was stirred for one hour at -20° C. At the same temperature, to the reaction solution was added 7-methoxy-3-(4-methoxyphenyl)-3-methylthiochroman-4-one (550 mg, 1.75 mmol), as obtained in Example 26, dissolved in tetrahydrofuran (20 ml), and then the mixture was stirred for 24 hours at -10° C. When the reaction is completed, saturated ammonium chloride solution 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=9:1) to obtain 946 mg (yield: 95%) of the title compound as a white solid.

Workup

  1. customas obtained in Example 26
  2. stirringthe mixture was stirred for 24 hours at -10° C
  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=9:1)

Sources & evidence

ORD record
ord-0372cb57b4f34299a56c16d78298bd41
Source dataset
uspto-grants-2000_11
Patent number
US06153768

Reaction notes

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