Sodium Phosphate, Dibasic → HCID 9863575, compound

HRID 2217641Notes

Reaction equation

HRID 2217641 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[N:20](S(C2C=CC(OC)=CC=2)(=O)=O)[CH:19]=1.P([O-])([O-])(O)=O.[Na+].[Na+].[Cl-].[NH4+]>CO>[OH:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][C:18]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[NH:20][CH:19]=1

Participants

5

Reactant 3

HCID 24203Sodium Phosphate, DibasicHCID 25517Ammonium ChlorideHCID 11386963HCID 11386963, compound

Product 1

HCID 9863575HCID 9863575, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(16-hydroxyhexadecyl)-1-(4-methoxybenzenesulfonyl)indole (400 mg, 0.72 mmol) dissolved in 20 ml of dry methanol were added disodium hydrogen-phosphate(205 mg, 1.44 mmol) and amalgam chloride(6%, 4g) at 0° C. under argon gas. After the resulting mixture was allowed to stand at room temperature for 12 hours, 50 mL of ammonium chloride was added thereto. The resulting mixture was extracted three times with 60 ml of ethyl ether. The combined organic layer was washed with saline, dried over anhydrous magnesium sulfate and then concentrated. The residue was purified by chromatography on a silica gel column to give 3-(16-hydroxyhexadecyl)indole (Compound 1) as a white solid (204 mg, 75%).

Workup

  1. extractionThe resulting mixture was extracted three times with 60 ml of ethyl ether
  2. washThe combined organic layer was washed with saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography on a silica gel column

Sources & evidence

ORD record
ord-94a38b75af3c4881a90c54a149b2a98e
Source dataset
uspto-grants-2008_08
Patent number
US07407983B2

Reaction notes

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