Methyl iodide → HCID 67882871, compound

HRID 1590407Notes

Reaction equation

HRID 1590407 reaction equation
F/[C:2](=[CH:5]\[C@@H:6]1[CH2:8][C@H:7]1[C:9]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]([Cl:16])[CH:10]=1)/[CH:3]=[O:4].[CH3:17][Mg]I.[Mg].CI>CCOCC>[Cl:16][C:11]1[CH:10]=[C:9]([C@@H:7]2[CH2:8][C@H:6]2/[CH:5]=[CH:2]\[CH:3]([OH:4])[CH3:17])[CH:14]=[CH:13][C:12]=1[Cl:15]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 5462224MagnesiumHCID 18651183HCID 18651183, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 67882871HCID 67882871, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

(±)-(2Z)-2-Fluoro-3-[trans-2-(3,4-dichlorophenyl)cyclopropyl]prop-2-enal (2.59 g) (example 19) in ehter (10 ml) was treated at 0° under nitrogen with methyl magnesium iodide, prepared from magnesium turning (0.26 g) and methyl iodide (0.7 ml) in ether (20 ml). After 18 hours at 25° the mixture was worked up as usual. Purification by chromatography (silica, ether/hexane) gave (±)-(3Z)-4-[trans-2-(3,4-dichlorophenyl)cyclopropyl]but-3-en-2-ol (2.0 g). NMR 1H: 7.23(1H,d), 7.05(1H,d), 6.90(1H,dd), 4.52(1H,m), 4.23(1H,m), 3.0(1H,s), 1.80(2H,m), 1.35(3H,d), 1.18(2H,m).

Workup

  1. customPurification by chromatography (silica, ether/hexane)

Sources & evidence

ORD record
ord-092bf833de8a4b72b426c4f5255ff9d7
Source dataset
uspto-grants-1993_04
Patent number
US05202356

Reaction notes

Loading…