Tributylstannane → 3-(Perfluoroisopropyl)propanol

HRID 1879611Notes

Reaction equation

HRID 1879611 reaction equation
[F:1][C:2]([C:12]([F:15])([F:14])[F:13])([C:8]([F:11])([F:10])[F:9])[CH2:3][CH:4](I)[CH2:5][OH:6].C([SnH](CCCC)CCCC)CCC>>[F:1][C:2]([C:12]([F:13])([F:14])[F:15])([C:8]([F:9])([F:11])[F:10])[CH2:3][CH2:4][CH2:5][OH:6]

Participants

3

Reactant 2

HCID 5948TributylstannaneHCID 27826014,5,5,5-Tetrafluoro-2-iodo-4-(trifluoromethyl)pentan-1-ol

Product 1

HCID 5427393-(Perfluoroisopropyl)propanol

Procedure

In accordance with scheme (9) above, a 500 mL two neck round bottom flask can be equipped with a thermocouple, agitator, and heating mantle. About 212.1 g (0.599 mole) 4,5,5,5-tetrafluoro-4(trifluoromethyl)-2-iodopentan-1-ol (212.1 g, 0.599 mole) can be added to the flask and heated to about 60° C. to 70° C. From a 100 mL pressure equalized addition funnel, about 196.4 g (0.675 mole) tributyltin hydride can be added drop-wise over a 4 hour period followed by 2 hours of continued heating and stirring. The RF-intermediate 4,5,5,5-tetrafluoro-4(trifluoromethyl)pentan-1-ol can be obtained through vacuum distillation and verified by gas chromatography/mass spectrometry (m/z 228 (M+), 211 (M+−OH), 159 (M+−CF3)).

Workup

  1. temperatureheating mantle
  2. temperatureheated to about 60° C. to 70° C
  3. additionaddition funnel
  4. temperatureof continued heating

Sources & evidence

ORD record
ord-2a20bff4a2a34a248c52da427cf1e4f1
Source dataset
uspto-grants-2012_11
Patent number
US08318656B2

Reaction notes

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