Pyridine → HCID 19029783, compound

HRID 2260161Notes

Reaction equation

HRID 2260161 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
  5. customThe residue obtained
  6. customis purified by chromatography on a silica column
  7. washeluted with a mixture of hexane and dichloromethane (90:10)
  8. customAfter evaporation of the solvents, 1.8 g (77%) of the expected product
  9. customare collected in the form of a yellow oil

Sources & evidence

ORD record
ord-25563b4a17ea499bb09aedf87452ddf0
Source dataset
uspto-grants-1995_12
Patent number
US05476860

Reaction notes

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