Diethyl Ether → 3-Ethynyl-1-iodooct-1-en-3-ol

HRID 2083680Notes

Reaction equation

HRID 2083680 reaction equation
[I:1][CH:2]=[CH:3][CH:4]([OH:10])[CH2:5][CH2:6][CH2:7][CH2:8][CH3:9].[C:11]([Mg]Br)#[CH:12].CCOCC>O1CCCC1>[C:11]([C:4]([OH:10])([CH2:5][CH2:6][CH2:7][CH2:8][CH3:9])[CH:3]=[CH:2][I:1])#[CH:12]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 534202231-Iodo-1-octen-3-olHCID 178418486HCID 178418486, compound

Product 1

HCID 541145263-Ethynyl-1-iodooct-1-en-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

As shown in FIG. 1, 1-iodo-1-octen-3-ol (II) is treated with an ethynyl Grignard reagent, conveniently ethynyl magnesium bromide, in a suitable Grignard solvent of the ether type, conveniently tetrahydrofuran, at reduced temperature, conveniently 0° C., while stirring for a short time, conveniently 1 hour, to give dl-3-ethynyl-1-iodo-1-octen-3-ol (III).

Sources & evidence

ORD record
ord-fa263440c18a468ea0a0ef2e84ffe312
Source dataset
uspto-grants-1978_04
Patent number
US04086269

Reaction notes

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