1-Octyne → 4-(Oct-1-yn-1-yl)benzaldehyde

HRID 735908Notes

Reaction equation

Br[C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1.[CH:10]#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]>>[C:10]([C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][CH:3]=1)#[C:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

Reactant 2

HCID 123701-Octyne

HCID 707414-Bromobenzaldehyde

Product 1

HCID 136885034-(Oct-1-yn-1-yl)benzaldehydeYield 84%

Procedure

The same procedure as employed in the preparation of Example 275 (step a) but using 4-bromobenzaldehyde and 1-octyne gave the title compound as a yellow oil (84%). 1H NMR (CDCl3, 300 MHz) δ 9.97 (s, 1H), 7.78 (d, 2H, J=8.3 Hz), 7.51 (d, 2H, J=8.3 Hz), 2.42 (t, 2H, J=7.0 Hz), 1.67-1.54 (m, 2H), 1.50-1.24 (m, 6H), 0.89 (m, 3H). M−(LC/MS(ESI)): 215.4. HPLC (Condition A), Rt: 5.17 min (HPLC purity: 78.6%).

Workup

customThe same procedure as employed in the preparation of Example 275 (step a) but

Sources & evidence

ORD record: ord-4a63fc343f064d22a2db5816c79850d3
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07592477B2

Reaction notes

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