Pyridine → HCID 19029783, compound

HRID 2256347Notes

Reaction equation

HRID 2256347 reaction equation
[OH:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]([OH:35])[C:21]2[CH:30]=[CH:29][C:28]3[C:27]([CH3:32])([CH3:31])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]=3[CH:22]=2)[CH:15]=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].C1C[O:39][CH2:38][CH2:37]1.N1C=CC=CC=1.C(Cl)(=O)C>O>[OH:1][C:2]1[CH:17]=[C:16]([O:18][CH2:19][CH:20]([C:21]2[CH:30]=[CH:29][C:28]3[C:27]([CH3:31])([CH3:32])[CH2:26][CH2:25][C:24]([CH3:34])([CH3:33])[C:23]=3[CH:22]=2)[O:35][C:38](=[O:39])[CH3:37])[CH:15]=[CH:14][C:3]=1[C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5]

Participants

6

Reactant 4

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 8028TetrahydrofuranHCID 19029751HCID 19029751, compound

Product 1

HCID 19029783HCID 19029783, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.2 g (4.6 mmol) of benzyl 2-hydroxy-4-[2-hydroxy-2-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)ethoxy]benzoate, 50 ml of THF and 380 μl (4.6 mmol) of pyridine are introduced into a flask. 330 μl (4.6 mmol) of acetyl chloride are added dropwise and the reaction mixture is stirred at room temperature for 8 hours. It is poured into water and extracted with ethyl ether, and the organic phase is separated, dried over magnesium sulphate and evaporated-The residue obtained is purified by chromatography on a silica column, eluted with a mixture of hexane and dichloromethane (90:10). After evaporation of the solvents, 1.8 g (77%) of the expected product are collected in the form of a yellow oil.

Workup

  1. extractionextracted with ethyl ether
  2. customthe organic phase is separated
  3. dry with materialdried over magnesium sulphate
  4. customevaporated-The residue obtained
  5. customis purified by chromatography on a silica column
  6. washeluted with a mixture of hexane and dichloromethane (90:10)
  7. customAfter evaporation of the solvents, 1.8 g (77%) of the expected product
  8. customare collected in the form of a yellow oil

Sources & evidence

ORD record
ord-7c6956ed204a4a9fb0e6a4e11f8777b6
Source dataset
uspto-grants-1997_08
Patent number
US05654331

Reaction notes

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