Pyridine → HCID 178475432, compound

HRID 1464831Notes

Reaction equation

HRID 1464831 reaction equation
[CH:1]1([Ti:6]([CH:25]2[CH:29]=[CH:28][CH:27]=[CH:26]2)([C:16]2[C:21]([F:22])=[CH:20][CH:19]=[C:18]([OH:23])[C:17]=2[F:24])[C:7]2[C:12]([F:13])=[CH:11][CH:10]=[C:9]([OH:14])[C:8]=2[F:15])[CH:5]=[CH:4][CH:3]=[CH:2]1.N1C=CC=CC=1.[C:36](OC(=O)C)(=[O:38])[CH3:37].[CH3:43][CH2:44][O:45]CC>C1(C)C=CC=CC=1.CN(C=O)C.O>[CH:25]1([Ti:6]([CH:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)([C:7]2[C:12]([F:13])=[CH:11][CH:10]=[C:9]([O:14][C:44](=[O:45])[CH3:43])[C:8]=2[F:15])[C:16]2[C:21]([F:22])=[CH:20][CH:19]=[C:18]([O:23][C:36](=[O:38])[CH3:37])[C:17]=2[F:24])[CH:29]=[CH:28][CH:27]=[CH:26]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 3283Diethyl EtherHCID 7918Acetic AnhydrideHCID 178516123HCID 178516123, compound

Product 1

HCID 178475432HCID 178475432, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21735183Dimethylformamide tolueneSolvent

Procedure

8.7 g (0.020 mol) of bis(cyclopentadienyl)bis(2,6-difluoro-3-hydroxyphenyl)titanium and 3.8 (0.048 mol) of pyridine in 30 ml of toluene/DMF mixture (1:1) are introduced into a 100 ml sulfation flask under nitrogen as protective gas. 4.9 g (0.048 mol) of acetic anhydride are added dropwise to this solution at room temperature over the course of 5 minutes, and the mixture is stirred for a further 24 hours (reaction check using thin-layer chromatography). The reaction mixture is then poured into ether and water. The ether phase is separated off, washed three times with water, dried using magnesium sulfate and evaporated on a rotary evaporator. The residue is purified by flash chromatography using a hexane/ether mixture 1:1 and, after evaporation, crystallized from an ether/hexane mixture. 7.7 g of a yellow powder of melting point 104°-123° C. (decomposition) are obtained.

Workup

  1. custom(reaction check using thin-layer chromatography)
  2. customThe ether phase is separated off
  3. washwashed three times with water
  4. customdried
  5. customevaporated on a rotary evaporator
  6. customThe residue is purified by flash chromatography
  7. customafter evaporation
  8. customcrystallized from an ether/hexane mixture

Sources & evidence

ORD record
ord-cefc77b2d8754c56aed7decb94005eb8
Source dataset
uspto-grants-1994_04
Patent number
US05306600

Reaction notes

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