Sodium Iodide → HCID 20058695, compound

HRID 2050649Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]#[C:11][CH2:12][CH2:13][CH2:14]O.CS(Cl)(=O)=O.[I-:21].[Na+]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[C:5]([F:9])=[CH:4][C:3]=1[C:10]#[C:11][CH2:12][CH2:13][CH2:14][I:21]

Participants

Reactant 3

HCID 5238Sodium Iodide

HCID 31297Methanesulfonyl chloride

HCID 20058693HCID 20058693, compound2×

Product 1

HCID 20058695HCID 20058695, compound

Procedure

Reacting 5-(2,4,5-trifluorophenyl)-4-pentyn-1-ol (Compound 43) with methanesulfonyl chloride and sodium iodide gives 5-(2,4,5-trifluorophenyl)-1-iodo-4-pentyne. Treatment of this iodide with zinc and copper cyanide, as in Example 2, gives the corresponding mixed cuprate. Addition of this cuprate to 4-[(3-oxo-4,4,4-trifluoro)-1-butynyl]-2-trimethylsilylfuran (Compound 37) and hydrogenating the adduct gives 4-[1-(2-oxo-3,3,3-trifluoro)propyl-6-(2,4,5-trifluorophenyl)]hexyl-2-trimethylsilylfuran (Compound 44). Oxidizing this furan (Compound 44) with singlet oxygen gives 4-[1-(2-oxo-3,3,3-trifluoro)propyl-6-(2,4,5-trifluorophenyl)]hexyl-5-hydroxy-2(5H)-furanone (Compound 14).

Sources & evidence

ORD record: ord-6ab9118ef489462ba5d7df56a4521302
Source dataset: uspto-grants-1991_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05013850

Reaction notes

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