Pyridine → HCID 178443445, compound

HRID 1464832Notes

Reaction equation

HRID 1464832 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.N1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[C:36](Cl)(=[O:46])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45].CC[O:50]CC.[C:53]1(C)C=[CH:57][CH:56]=[CH:55][CH:54]=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:36](=[O:46])[CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])[C:8]=2[F:15])[C:16]2[C:21]([F:22])=[CH:20][CH:19]=[C:18]([O:23][C:31](=[O:50])[CH2:32][CH2:33][CH2:34][CH2:35][CH2:53][CH2:54][CH2:55][CH2:56][CH3:57])[C:17]=2[F:24])[CH:29]=[CH:28][CH:27]=[CH:26]1

Participants

7

Reactant 5

HCID 1049PyridineHCID 3283Diethyl EtherHCID 66982Decanoyl chlorideHCID 21735183Dimethylformamide tolueneHCID 178516123HCID 178516123, compound

Product 1

HCID 178443445HCID 178443445, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

6.1 g (0.014 mol) of bis(cyclopentadienyl)bis(2,6-difluoro-3-hydroxyphenyl)titanium and 2.7 g (0.0336 mol) of pyridine in 50 ml of a toluene/DMF mixture (1:1) are introduced into a 100 ml sulfation flask under nitrogen as protective gas. 6.4 g (0.0336 mol) of decanoyl chloride are added dropwise to this red solution at room temperature over the course of 5 minutes, and the mixture is stirred for a further 16 hours (reaction check using thin-layer chromatography). The reaction mixture is then poured into ether and water. The ether phase is evaporated off, washed twice with water, dried using magnesium sulfate and evaporated on a rotary evaporator. The residue is purified by flash chromatography using a hexane/ether mixture 9:1 as eluent, and evaporated on a rotary evaporator. 6.9 g of a red, clear resin are obtained.

Workup

  1. custom(reaction check using thin-layer chromatography)
  2. customThe ether phase is evaporated off
  3. washwashed twice with water
  4. customdried
  5. customevaporated on a rotary evaporator
  6. customThe residue is purified by flash chromatography
  7. customevaporated on a rotary evaporator
  8. custom6.9 g of a red, clear resin are obtained

Sources & evidence

ORD record
ord-644cb700e3134ca4985085b36b4150d7
Source dataset
uspto-grants-1994_04
Patent number
US05306600

Reaction notes

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