Methanol → 4,4,5,5,6,6,7,7,7-Nonafluoro-1-heptanol

HRID 1267466Notes

Reaction equation

HRID 1267466 reaction equation
[F:1][C:2]([F:18])([C:8]([F:17])([F:16])[C:9]([F:15])([F:14])[C:10]([F:13])([F:12])[F:11])[CH2:3][CH2:4][C:5](O)=[O:6].CO>O1CCCC1>[F:1][C:2]([F:18])([C:8]([F:16])([F:17])[C:9]([F:14])([F:15])[C:10]([F:11])([F:12])[F:13])[CH2:3][CH2:4][CH2:5][OH:6]

Participants

4

Reactant 2

HCID 887MethanolHCID 108035372H,2H,3H,3H-Perfluoroheptanoic acid

Product 1

HCID 27790914,4,5,5,6,6,7,7,7-Nonafluoro-1-heptanolYield 97.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulfide complex (5.2 ml, 52.2 mmol) was slowly added to a solution of 4,4,5,5,6,6,7,7,7-nonafluoroheptanoic acid (5.10 g, 17.4 mmol) in anhydrous tetrahydrofuran (50 ml) at −50° C. The reaction mixture was stirred for 4 hours at room temperature and cooled to 0° C., followed by addition of methanol. After distilling off the solvent, the residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/5→1/3) to give 4,4,5,5,6,6,7,7,7-nonafluoroheptan-1-ol (4.7 g, Yield 97%) as a colorless oil.

Workup

  1. temperaturecooled to 0° C.
  2. distillationAfter distilling off the solvent
  3. customthe residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=1/5→1/3)

Sources & evidence

ORD record
ord-7b236f7e7bf1494d9b2f021702089805
Source dataset
uspto-grants-2003_04
Patent number
US06552069B1

Reaction notes

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