Dimethylformamide → 3-[(2,2,3,3,4,4,4-Heptafluorobutoxy)methyl]-3-methyloxetane

HRID 1488715Notes

Reaction equation

HRID 1488715 reaction equation
[H-].[Na+].[F:3][C:4]([F:14])([C:7]([F:13])([F:12])[C:8]([F:11])([F:10])[F:9])[CH2:5][OH:6].[OH:15][CH2:16][C:17]1[CH:18]=C(C)C=C[C:22]=1S([O-])(=O)=O.[CH3:28]N(C)C=O>>[F:3][C:4]([F:14])([C:7]([F:12])([F:13])[C:8]([F:9])([F:10])[F:11])[CH2:5][O:6][CH2:22][C:17]1([CH3:18])[CH2:28][O:15][CH2:16]1

Participants

5

Reactant 4

HCID 6228Dimethylformamide2×HCID 9776HeptafluorobutanolHCID 24758Sodium hydrideHCID 22906193HCID 22906193, compound

Product 1

HCID 220152663-[(2,2,3,3,4,4,4-Heptafluorobutoxy)methyl]-3-methyloxetane

Procedure

A 50 weight percent dispersion of sodium hydride 6.1 grams (127 mmol) in mineral oil, was washed twice with hexanes and was suspended in 60 milliliters of dimethyl formamide. Then 24.0 grams (120 mmol) of 2,2,3,3,4,4,4-heptafluorobutan-1-ol was added and mixture was stirred for 45 minutes. A solution of 25.0 grams (97.5 mmol) of 3-hydroxymethyl-p-toluenesulfonate in 15 milliliters of dimethyl formamide was added and the mixture was heated at 75°-85° C. for 30 hours when 1HNMR analysis of an aliquot showed that the starting sulfonate had been consumed.

Workup

  1. temperaturethe mixture was heated at 75°-85° C. for 30 hours when 1HNMR analysis of an aliquot
  2. customhad been consumed

Sources & evidence

ORD record
ord-c580343620644b1c8a76eeb91cda64c6
Source dataset
uspto-grants-1997_10
Patent number
US05674951

Reaction notes

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