Tributylamine → HCID 15113981, compound

HRID 2249013Notes

Reaction equation

HRID 2249013 reaction equation
C(N(CCCC)CCCC)CCC.[FH:14].[F:15][C:16]1[C:21]([CH:22]2[O:24][CH2:23]2)=[C:20]([F:25])[C:19]([F:26])=[C:18]([F:27])[C:17]=1[F:28]>>[F:14][CH:22]([C:21]1[C:16]([F:15])=[C:17]([F:28])[C:18]([F:27])=[C:19]([F:26])[C:20]=1[F:25])[CH2:23][OH:24]

Participants

4

Reactant 3

HCID 7622Tributylamine2×HCID 14917Hydrofluoric AcidHCID 27759812-(2,3,4,5,6-Pentafluorophenyl)oxirane

Product 1

HCID 15113981HCID 15113981, compoundYield 31.9%

Conditions

Temperature
40 °C

Procedure

To Teflon vessel containing 4.2 g (22.5 mmol)of tributylamine was cooled in a dry-ice methanol bath, and to this was added dropwise 2.3 g (112.5 mmol) of anhydrous hydrogen fluoride to prepare 6.4 g (22.5 mmol) of n-Bu3N.5HF. To this was added dropwise 3.15 g (15 mmol) of (+)-pentafluorostyrene oxide at 0° C., and was stirred for 10 hours at 40° C. After it was left to cool, the same treatment as that provided in Example 16 gave 1.1 g of (+)-2-fluoro-2-(pentafluorophenyl)ethanol. Its GC purity was 96%, while its [α]D25 was +10.8° (c=0.54, CHCl3).

Workup

  1. temperaturewas cooled in a dry-ice methanol bath
  2. waitAfter it was left
  3. temperatureto cool
  4. customthe same treatment as that provided in Example 16

Sources & evidence

ORD record
ord-6ccf8177470244969e36bb77eacc33b8
Source dataset
uspto-grants-1991_08
Patent number
US05041641

Reaction notes

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