Triethylamine → 3-(1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl)propyl prop-2-enoate

HRID 1993290Notes

Reaction equation

HRID 1993290 reaction equation
[F:1][C:2]([F:20])([S:13]([CH2:16][CH2:17][CH2:18][OH:19])(=[O:15])=[O:14])[C:3]([F:12])([F:11])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6].C(N(CC)CC)C.[Cl-].[Ca+2].[Cl-].[C:31](Cl)(=[O:34])[CH:32]=[CH2:33]>C(C1C=C(O)C(=CC=1)O)(C)(C)C.ClCCl>[C:31]([O:19][CH2:18][CH2:17][CH2:16][S:13]([C:2]([F:1])([F:20])[C:3]([F:11])([F:12])[C:4]([F:10])([F:9])[C:5]([F:8])([F:7])[F:6])(=[O:15])=[O:14])(=[O:34])[CH:32]=[CH2:33]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 5284359Calcium ChlorideHCID 714036003-(1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl)propan-1-ol

Product 1

HCID 714137873-(1,1,2,2,3,3,4,4,4-Nonafluorobutane-1-sulfonyl)propyl prop-2-enoateYield 95.3%

Reagents, catalysts & solvents 2

HCID 73814-tert-ButylcatecholCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of 3-(perfluorobutylsulfonyl)propanol (54.4 g, 159 mmol), triethylamine (33 ml, 238 mmol), 4-t-butylcatechol (0.14 g) and dichloromethane (520 ml) was cooled to 0° C. in a state of being equipped with a calcium chloride, and then acryloyl chloride (15.5 ml, 191 mmol) was slowly added dropwise over 40 minutes. After stirring at room temperature for one hour and washing the mixture with 15% citric acid (600 ml) water and saturated saline, the mixture was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure to obtain a crude acrylate ester. The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1) and the transparent liquid was vacuum-dried after concentration to obtain 60.0 g of 3-(perfluorobutylsulfonyl)propyl acrylate. Yield was 95.3%.

Workup

  1. washwashing the mixture with 15% citric acid (600 ml) water and saturated saline
  2. dry with materialthe mixture was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customto obtain a crude acrylate ester
  6. customThe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=6:1)
  7. customthe transparent liquid was vacuum-dried
  8. concentrationafter concentration

Sources & evidence

ORD record
ord-817995fa7c7f43648197b7e6530b4037
Source dataset
uspto-grants-2010_01
Patent number
US07651993B2

Reaction notes

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