Ammonium Chloride → 4-[9-(t-Butyldimethylsilyloxy)-4,7-dioxa-1-nonynyl]-4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman

HRID 1792381Notes

Reaction equation

HRID 1792381 reaction equation
[Si:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O: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][S:34]2)=[CH:29][CH:28]=1.[Cl-].[NH4+]>O1CCCC1>[Si:1]([O:8][CH2:9][CH2:10][O:11][CH2:12][CH2:13][O: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)[S: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]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 220332467-Methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman-4-oneHCID 235380372,2,3,3-Tetramethyl-4,7,10-trioxa-3-silatridec-12-yneHCID 178418339Butyllithium

Product 1

HCID 235379634-[9-(t-Butyldimethylsilyloxy)-4,7-dioxa-1-nonynyl]-4-hydroxy-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochromanYield 68.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-20 °C

Procedure

To a solution of 9-(t-butyldimethylsilyloxy)-4,7-dioxa-1-nonyne (1.03 g, 4.01 mmol) in dry tetrahydrofuran (10 ml) was added dropwise -n-butyl lithium (2.3 ml, 3.74 mmol, 1.63 mole/l in tetrahydrofuran) at −78° C., which was then stirred at −20° C. for 1 hour. Then, to this reaction mixture was added 7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman-4-one (1.0 g, 2.67 mmol) dissolved in tetrahydrofuran (10 ml) at the same temperature for 30 min, and the resulting mixture was stirred at −10° C. (for 24 hours. After the reaction was completed, saturated ammonium chloride solution was added to the reaction solution, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was subjected to column chromatography (n-hexane:ethyl acetate=4:1) to give the title compound (1.15 g, yield: 68%) as a colorless oil.

Workup

  1. stirringthe resulting mixture was stirred at −10° C. (for 24 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. dry with materialThe extract was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-985ad99cf9e547d79a98f2f0c6090a19
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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