1-Octyne → 3-(1-Octynyl)furan-2-carboxaldehyde

HRID 569485

Reaction equation

Br[C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH:7]=[O:8].[CH:9]#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]>>[C:9]([C:2]1[CH:6]=[CH:5][O:4][C:3]=1[CH:7]=[O:8])#[C:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

Reactant 2

HCID 123701-Octyne

HCID 33672713-Bromo-2-furaldehyde

Product 1

HCID 201471613-(1-Octynyl)furan-2-carboxaldehydeYield 72%

Procedure

Reaction of 3-bromofuran-2-carboxaldehyde (4.71 g, 27 mmole from Example 5) with 1-octyne (3 g, 27 mmole) as described in Example 8 afforded 3.96 g (72%) of the title compound, as an oil, after chromatography on silica (DCM:Hexane 1:2), νmax (film) 2950, 2930, 2850, 2230, 1680, 1570, 1420, 1360, 1275, 890, 775 cm-1 ; δ(CDCl3) 0.92(3H, distorted t), 1.42(8H, complex m), 2.48(2H, t, J=6.5 Hz), 6.59(1H, d, J=3 Hz), 7.62(1H, d, J=3 Hz), 9.82(1H, s).

Sources & evidence

ORD record: ord-86ad530678744e9ba740ea1c3f63fa1c
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04732901

Linked notes

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