Palmitoyl chloride → HCID 20280069, compound

HRID 1247922Notes

Reaction equation

HRID 1247922 reaction equation
[OH:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.C(N(CC)CC)C.[C:16](Cl)(=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]>O1CCCC1>[C:16]([O:1][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1)(=[O:32])[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 8206Palmitoyl chlorideHCID 8471TriethylamineHCID 114724-Hydroxymethylpyridine

Product 1

HCID 20280069HCID 20280069, compoundYield 44.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-hydroxymethylpyridine (10.02 g) and triethylamine (9.27 g) in tetrahydrofuran (100 ml) was dropped a solution of hexadecanoyl chloride (25.2 g) in tetrahydrofuran (80 ml) under cooling in an ice bath and stirring, which was continued for one hour at the same temperature. A resulting precipitate was filtered off and the filtrate was evaporated to dryness. The residue was dissolved in diether ether, washed with water, dried over magnesium sulfate and evaporated. The residue was purified by column chromatography on silica gel (250 g) using methylene chloride-ethyl acetate as an eluent to give 4-hexadecanoyloxymethylpyridine (14.3 g).

Workup

  1. temperatureunder cooling in an ice bath
  2. filtrationA resulting precipitate was filtered off
  3. customthe filtrate was evaporated to dryness
  4. dissolutionThe residue was dissolved in diether ether
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customThe residue was purified by column chromatography on silica gel (250 g)

Sources & evidence

ORD record
ord-e2d0c73facb443a5b896f0af22624538
Source dataset
uspto-grants-1985_06
Patent number
US04521413

Reaction notes

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