Triethylamine → HCID 54050382, compound

HRID 1416794Notes

Reaction equation

HRID 1416794 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.C(N(CC)CC)C.[F:27][C:28]([C:73]([F:76])([F:75])[F:74])([O:32][C:33]([F:72])([F:71])[C:34]([F:70])([C:66]([F:69])([F:68])[F:67])[O:35][C:36]([F:65])([F:64])[C:37]([F:63])([C:59]([F:62])([F:61])[F:60])[O:38][C:39]([F:58])([F:57])[C:40]([F:56])([C:52]([F:55])([F:54])[F:53])[O:41][C:42]([F:51])([F:50])[C:43]([F:49])([F:48])[C:44]([F:47])([F:46])[F:45])[C:29](F)=[O:30]>>[F:27][C:28]([C:73]([F:74])([F:75])[F:76])([O:32][C:33]([F:71])([F:72])[C:34]([F:70])([C:66]([F:67])([F:68])[F:69])[O:35][C:36]([F:64])([F:65])[C:37]([F:63])([C:59]([F:62])([F:61])[F:60])[O:38][C:39]([F:57])([F:58])[C:40]([F:56])([C:52]([F:55])([F:54])[F:53])[O:41][C:42]([F:51])([F:50])[C:43]([F:49])([F:48])[C:44]([F:47])([F:46])[F:45])[C:29]([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:30]

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 118188Perfluoro-2,5,8,11-tetramethyl-3,6,9,12-tetraoxapentadecanoyl fluorideHCID 22677161HCID 22677161, compound

Product 1

HCID 54050382HCID 54050382, compoundYield 71.8%

Procedure

A 50 mL round bottom flask equipped with a magnetic stirring bar and an addition funnel was charged with 6.2 g of 98% (3-hydroxypropyl)heptamethylcyclotetrasiloxane (18 mmoles) and 1.8 g of triethylamine (18 mmoles). The mixture was stirred and 15.0 g of 95% perfluoro-2,5,8,11-tetramethyl-3,6,9,12-tetraoxapentadecanoyl fluoride (17 mmoles) was added dropwise. After complete addition of the acid fluoride a gas chromatographic analysis indicated that essentially all of the acid fluoride and most of the cyclosiloxane were consumed with predominately the formation of one product. A 25 mL portion of dilute hydrochloric acid was added to the flask and the two phase mixture was transferred into a separatory funnel and the aqueous layer was separated from the siloxane layer. The siloxane layer was washed with two 25 mL portions of water and the siloxane layer was transferred into a 50 mL round bottom flask and distilled at 118-28° C. and 0.05 mmHg to yield a fraction of 14.0 g (71% yield) of 99% [3-(perfluoro-2,5,8,11-tetramethyl-3,6,9,12-tetraoxapentadecan-oyl)oxypropyl]heptamethylcyclotetrasiloxane (12.2 mmoles), which corresponds to formula (I) wherein m is 1, n is 3, X is OC(O), and RF is given by formula (II) wherein p is 4, or more specifically as shown in formula (VII) wherein p=4. The product was analyzed by spectroscopy with the following results: 1H NMR 400 MHz, CDCl3 : d 0.1 (s 21 H), 0.6 (t 2 H), 1.8 (p 2 H), 4.4 (m 2 H); IR (neat liquid on NaCl): cm 2970 (m), 1780 (s), 1245 (vs), 1200 (s), 1145 (s), 1070 (vs), 995 (s), 970 (s), 810 (vs), 750 (m).

Workup

  1. customA 50 mL round bottom flask equipped with a magnetic stirring bar and an addition funnel
  2. custommost of the cyclosiloxane were consumed with predominately the formation of one product
  3. additionA 25 mL portion of dilute hydrochloric acid was added to the flask
  4. customthe two phase mixture was transferred into a separatory funnel
  5. customthe aqueous layer was separated from the siloxane layer
  6. washThe siloxane layer was washed with two 25 mL portions of water
  7. customthe siloxane layer was transferred into a 50 mL round bottom flask
  8. distillationdistilled at 118-28° C.

Sources & evidence

ORD record
ord-cb1c2828a5bf4749b9a8ad773ecd1f66
Source dataset
uspto-grants-1999_06
Patent number
US05914420

Reaction notes

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