Pyridine → HCID 86754127, compound

HRID 1416795Notes

Reaction equation

HRID 1416795 reaction equation
[OH:1][CH2:2][CH2:3][CH2:4][Si:5]1([CH3:19])[O:12][Si:11]([CH3:14])([CH3:13])[O:10][Si:9]([CH3:16])([CH3:15])[O:8][Si:7]([CH3:18])([CH3:17])[O:6]1.N1C=CC=CC=1.[F:26][C:27]([F:50])([C:31]([F:49])([F:48])[C:32]([F:47])([F:46])[C:33]([F:45])([F:44])[C:34]([F:43])([F:42])[C:35]([F:41])([F:40])[C:36]([F:39])([F:38])[F:37])[C:28](Cl)=[O:29]>>[F:26][C:27]([F:50])([C:31]([F:48])([F:49])[C:32]([F:46])([F:47])[C:33]([F:44])([F:45])[C:34]([F:42])([F:43])[C:35]([F:41])([F:40])[C:36]([F:39])([F:38])[F:37])[C:28]([O:1][CH2:2][CH2:3][CH2:4][Si:5]1([CH3:19])[O:12][Si:11]([CH3:14])([CH3:13])[O:10][Si:9]([CH3:16])([CH3:15])[O:8][Si:7]([CH3:18])([CH3:17])[O:6]1)=[O:29]

Participants

4

Reactant 3

HCID 1049PyridineHCID 78978Perfluorooctanoyl chlorideHCID 22677161HCID 22677161, compound

Product 1

HCID 86754127HCID 86754127, compound

Procedure

A 25 mL round bottom flask equipped with a magnetic stirring bar and an addition funnel was charged with 4.0 g of (3-hydroxypropyl)heptamethylcyclotetrasiloxane (12 mmoles) and 1.0 g of pyridine (13 mmoles). The mixture was stirred and 5.0 g of perfluorooctanoyl chloride (12 mmoles) was added dropwise. After complete addition of the acid fluoride a gas chromatographic analysis indicated that essentially all of the acid chloride and most of the cyclosiloxane were consumed with one product as 96.5% of the mixture. The contents of the flask were filtered using a 0.45 micron syringe filter into a 50 mL 1-necked round bottom flask. The solids in the flask were washed with 2.5 mL of pentane and this suspension added to the syringe and filtered into the 50 mL flask. The solids in the syringe were washed with an additional 2.5 mL of pentane and filtered into the 50 mL flask. The contents of the flask were distilled at 82° C. and 0.04 mmHg to yield a fraction of [3-(perfluorooctanoyl)oxypropyl]-heptamethylcyclotetrasiloxane which corresponds to formula (I) wherein m is 1, n is 3, X is OC(O), and RF is a perfluorinated straight chain monovalent alkyl radical of 7 carbons atoms, or more specifically as shown in formula (VIII) below. ##STR9##

Workup

  1. customA 25 mL round bottom flask equipped with a magnetic stirring bar and an addition funnel
  2. custommost of the cyclosiloxane were consumed with one product as 96.5% of the mixture
  3. filtrationThe contents of the flask were filtered
  4. filtrationfilter into a 50 mL 1-necked round bottom flask
  5. washThe solids in the flask were washed with 2.5 mL of pentane
  6. additionthis suspension added to the syringe
  7. filtrationfiltered into the 50 mL flask
  8. washThe solids in the syringe were washed with an additional 2.5 mL of pentane
  9. filtrationfiltered into the 50 mL flask
  10. distillationThe contents of the flask were distilled at 82° C.

Sources & evidence

ORD record
ord-08f4821d3d164117862d8e6a7680aea0
Source dataset
uspto-grants-1999_06
Patent number
US05914420

Reaction notes

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