Pyridine → HCID 19885977, compound

HRID 654948Notes

Reaction equation

HRID 654948 reaction equation
[OH:1][CH:2]([C:16]1[CH:17]=[C:18]([Si:21]([CH3:24])([CH3:23])[CH3:22])[O:19][CH:20]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1.[C:25](OC(=O)C)(=[O:27])[CH3:26].N1C=CC=CC=1.CCCCCC>C(OCC)C.CCCCCC>[C:25]([O:1][CH:2]([C:16]1[CH:17]=[C:18]([Si:21]([CH3:22])([CH3:23])[CH3:24])[O:19][CH:20]=1)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]1[S:12][CH:13]=[CH:14][CH:15]=1)(=[O:27])[CH3:26]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8058HexaneHCID 19885932HCID 19885932, compound

Product 1

HCID 19885977HCID 19885977, compound

Reagents, catalysts & solvents 1

HCID 21584099Diethylether hexaneSolvent

Procedure

A solution of 4-(1-hydroxy-9-thiophen-2-ylnonyl)-2-trimethylsilylfuran (0.034 g, 0.093 mmol), acetic anhydride (1 ml) and pyridine (0.25 ml) was stirred at room temperature until no starting material was visible by TLC. The reaction mixture was concentrated and the residue taken up in ethyl ether, washed with 10% hydrochloric acid, saturated sodium chloride, aqueous 5% cupric sulfate solution, water, saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated to give a pale oil. Purificatioon by flash chromatography (silica, 100% hexane to 5% ethyl ether/hexane) gave the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washwashed with 10% hydrochloric acid, saturated sodium chloride, aqueous 5% cupric sulfate solution, water, saturated sodium chloride solution
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a pale oil

Sources & evidence

ORD record
ord-12bd0f99d6134ef19a67fccb1465a340
Source dataset
uspto-grants-1992_07
Patent number
US05134128

Reaction notes

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