Water → (-)-2-Fluoroheptanol

HRID 2291773Notes

Reaction equation

HRID 2291773 reaction equation
[O:1]1[CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:2]1.C1C=CN=CC=1.[FH:15].O>CCOCC>[F:15][CH:3]([CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])[CH2:2][OH:1]

Participants

5

Reactant 3

HCID 962WaterHCID 64774Pyridine, hydrofluoride (1:1)HCID 922152-Pentyloxirane

Product 1

HCID 15918973(-)-2-Fluoroheptanol

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 1.14 g (10.0 mM) of (+)-1,2-epoxyheptane ([α]D +15.1° (neat)) in 5 ml of dry ether was quickly added dropwise into ice-cooled 2 ml of hydrogen fluoride/pyridine. After the addition, the mixture was stirred for 30 minutes in an ice bath, followed by addition of 10 ml of cold water and 3 times of extraction with 10 ml of ether. The extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate, followed by drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distillation apparatus, to obtain 0.492 g of crude (-)-2-fluoroheptanol. Further, by repeating the above operations, 1.35 g of the crude product was obtained and rectified by means of a Claisen flask to obtain 0.80 g (600 mM) of objective (-)-2-fluoroheptanol. Yield: 20.0%. The product showed the following properties:

Workup

  1. additionAfter the addition
  2. washThe extract liquid was washed 3 times with 10 ml of 1N-sodium carbonate
  3. dry with materialby drying with anhydrous magnesium sulfate, removal of ether by vacuum distillation and distillation with Kugelrohr distillation apparatus

Sources & evidence

ORD record
ord-909527f21cc9484eab0400a555618c4c
Source dataset
uspto-grants-1989_01
Patent number
US04798680

Reaction notes

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