Boron trifluoride etherate → HCID 23039693, compound

HRID 2166406Notes

Reaction equation

HRID 2166406 reaction equation
[F:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH2:4][OH:5].[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[C:18]1([CH2:21][CH2:22][CH3:23])[O:20][CH2:19]1.B(F)(F)F.CCOCC>C(OCC)C>[Cl:10][C:11]1[CH:16]=[C:15]([Cl:17])[CH:14]=[CH:13][C:12]=1[C:18]([O:5][CH2:4][C:3]1[CH:6]=[CH:7][CH:8]=[CH:9][C:2]=1[F:1])([CH2:21][CH2:22][CH3:23])[CH2:19][OH:20]

Participants

5

Reactant 3

HCID 8000Boron trifluoride etherateHCID 679692-Fluorobenzylic alcoholHCID 230396712-(2,4-Dichlorophenyl)-2-propyloxirane

Product 1

HCID 23039693HCID 23039693, compoundYield 9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 11.6 g (92 mmoles) of 2-fluorobenzyl alcohol and 21.9 g (92 mmoles) of 2-(2,4-dichlorophenyl)-1,2-epoxypentane is added dropwise at 0°-2° C. to a solution of 2.0 ml (16.5 mmoles) of boron trifluoride ethyl etherate in 10 ml of diethyl ether. The solution is allowed to react further overnight at +7° C. and is worked up as in Example I by extraction and column chromatography. 2.95 g of the pure product are obtained in the form of a colourless oil. 100 MHz-1H-NMR (CDCl3): δ=6.8-7.7 ppm (m, 7H aromatic); 4.5 ppm (s, 2H, ##STR27## 3.9-4.4 ppm (m, 2H, --CH2OH); 1.7-2.3 ppm (m, 3H, --CH2CH2CH3 and OH); 0.7-1.4 ppm (m, 5H, --CH2CH3).

Workup

  1. customto react further overnight at +7° C.
  2. extractionis worked up as in Example I by extraction and column chromatography

Sources & evidence

ORD record
ord-a663e5308bfc4d47ae96b7b98297b283
Source dataset
uspto-grants-1990_07
Patent number
US04945100

Reaction notes

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