Methyl iodide → HCID 86733027, compound

HRID 1658647Notes

Reaction equation

HRID 1658647 reaction equation
[I-:1].[CH2:2]1[CH2:28][O:27][CH:5]([CH2:6][CH2:7][P+:8]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:4][O:3]1.[CH2:29]([Li])CCC.[I-].[PH4+].C1COC(CC=P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)CO1.CI>O1CCCC1.CCCCCC>[I-:1].[CH2:2]1[CH2:28][O:27][CH:5]([CH2:6][CH:7]([P+:8]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH3:29])[CH2:4][O:3]1

Participants

8

Reactant 5

HCID 6328Methyl iodideHCID 166618Phosphonium iodide ((PH4)I)HCID 86733029HCID 86733029, compoundHCID 86733031HCID 86733031, compoundHCID 178418339Butyllithium

Product 1

HCID 86733027HCID 86733027, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

1.51 g (3.0 mmol) of finely powdered (4-ethylenedioxybutyl)-triphenyl-phosphonium iodide are suspended in 10 ml of tetrahydrofuran and treated dropwise with a solution of 4.5 mmol of butyl-lithium in hexane. The solution turns red as the phosphonium iodide goes into solution as (4-ethylenedioxy-butylidene)-triphenyl-phosphorane. After approximately 10 minutes, 0.25 ml (4.5 mmol) of methyl iodide are added to this solution, which thereby becomes lighter, and the (4-ethylenedioxy-1-methylbutyl)-triphenyl-phosphonium iodide which is formed partially precipitates as an oil. After 10 minutes, 3.0 mmol of butyl-lithium in hexane are added dropwise and the solution thereby again becomes dark red.

Sources & evidence

ORD record
ord-7f64946cee534c09843f2bb70aa66724
Source dataset
uspto-grants-1976_06
Patent number
US03965198

Reaction notes

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