Iodine → HCID 19097835, compound

HRID 486324Notes

Reaction equation

HRID 486324 reaction equation
[CH:1]#[C:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14].C([Mg]Br)C.[I:19]I>CCOCC>[I:19][C:1]#[C:2][CH2:3][O:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH3:14]

Participants

5

Reactant 3

HCID 807IodineHCID 19097838HCID 19097838, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 19097835HCID 19097835, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Following the procedure described in Vaughn, T. H., J. Am. Chemical Soc'y 55 3456 (1933), 4-oxatetradecyne (13 g, 66.2 mmol) was reacted with ethylmagnesium bromide (73 mmol) in dry ether. The resulting alkynyl magnesiumbromide was reacted with iodine and provided 15 g of 1-iodo-4-oxa-tetradecyne as viscous liquid (71% yield). The sample was analyzed with 1H-NMR in CDCl3, and the observed chemical shift peaks were at δ=0.88 (t, 3H, --CH3), 1.23-1.4 (br singlet, 14H, --CH2 --), 1.57 (pentate center, 2H, --CH2 --), 3.51 (t, J=7.0 Hz, 2H, --CH2 --O), and 4.28 (s, 2H, O--CH2 --C≡C). Observed IR (KBr) peak was at 2120 (--C≡C--) cm-1 ; no peak was observed at 3298 (--C≡CH) cm-1.

Sources & evidence

ORD record
ord-ef6f9b3b1c57448ea4fab62aaca7a471
Source dataset
uspto-grants-1994_03
Patent number
US05290960

Reaction notes

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