Water → 4-(9-Hydroxynonyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

HRID 1792308Notes

Reaction equation

HRID 1792308 reaction equation
[Si]([O: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)[O: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.[NH+]1C=CC=CC=1.O>C(O)C>[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)[O: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

5

Reactant 3

HCID 962WaterHCID 4989215PyridiniumHCID 220330064-[9-(t-Butyldimethylsilyloxy)nonyl]-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman

Product 1

HCID 154817594-(9-Hydroxynonyl)-7-methoxymethoxy-3-(4-methoxymethoxyphenyl)-3-methylchromanYield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-[9-(t-Butyldimethylsilyloxy)nonyl]-7-methoxymet hoxy-3-(4-methoxymethoxyphenyl)-3-methylchroman (1.34 g, 2.23 mmol) was dissolved in ethanol (70 ml), and pyridinium ptoluenesulfonate (426 mg, 1.70 mmol) was added thereto. The reaction mixture was stirred at room temperature for 10 hours, water was added, and the resulting mixture was extracted with ethyl acetate. The organic layer was separated, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=7:3 and 1:1) to give the title compound (831 mg, yield 77%) as a colorless oil. In this reaction, 247 mg (18%) of the unreacted starting compound was recovered.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4c5ff6d47c4741639e7e9582c711852a
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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