Water → HCID 22033108, compound

HRID 1792316Notes

Reaction equation

HRID 1792316 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]#[C:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH2:29][O:30][CH3:31])=[CH:25][CH:26]=2)[S:21][CH2:20][C:19]1([C:33]1[CH:38]=[CH:37][C:36]([O:39][CH2:40][O:41][CH3:42])=[CH:35][CH:34]=1)[CH3:32])(C(C)(C)C)(C)C.[OH-].[Na+].COCCl.O>C(O)C.[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC>[OH:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH:18]1[C:27]2[C:22](=[CH:23][C:24]([O:28][CH2:29][O:30][CH3:31])=[CH:25][CH:26]=2)[S:21][CH2:20][C:19]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]

Participants

7

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 14798Sodium HydroxideHCID 22033070HCID 22033070, compound

Product 1

HCID 22033108HCID 22033108, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 702EthanolSolvent

Procedure

4-[9-(t-Butyldimethylsilyloxy)-1-nonynyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylthiochroman (1.43 g, 2.27 mmol) was dissolved in ethanol (100 ml) and tetrahydrofuran (10 ml), and 20% palladium hydroxide on carbon (500 mg) which had been washed with ethanol was added thereto. The reaction solution was stirred for 1 day under hydrogen (atmospheric pressure). Ethyl acetate was added to the reaction mixture, which was then filtered and concentrated. The concentrate was dissolved in dichloromethane (50 ml) and 1N-sodium hydroxide (2 ml), and tetra-n-butylammonium chloride (556 mg, 2 mmol) was added thereto at room temperature. To the reaction mixture was added dropwise methoxymethyl chloride (0.22 ml, 3 mmol) at the same temperature, which was then stirred for 2 hours. Water was added, and the resulting solution was extracted with ethyl acetate. Then, the organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=1:1) to give the title compound (855 mg, yield 75%) as a white solid.

Workup

  1. washtetrahydrofuran (10 ml), and 20% palladium hydroxide on carbon (500 mg) which had been washed with ethanol
  2. additionwas added
  3. additionEthyl acetate was added to the reaction mixture, which
  4. filtrationwas then filtered
  5. concentrationconcentrated
  6. dissolutionThe concentrate was dissolved in dichloromethane (50 ml)
  7. customat room temperature
  8. stirringwas then stirred for 2 hours
  9. extractionthe resulting solution was extracted with ethyl acetate
  10. washThen, the organic layer was washed with water and saturated sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2f286ed6f9e9461fb83980ce87cae00e
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

Loading…