1-Tridecyne → HCID 20147173, compound

HRID 569480

Reaction equation

HRID 569480 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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]>ClCCl>[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][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

4

Reactant 2

HCID 1177541-TridecyneHCID 33672713-Bromo-2-furaldehyde

Product 1

HCID 20147173HCID 20147173, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of 3-bromofuran-2-carboxaldehyde (3.86 g, 21.5 mmole, from Example 5) with 1-tridecyne (6.7 g) as described in Example 1 afforded 2.28 g (39% of the title compound after chromatography with dichloromethane on silica. Recrystallisation from petroleum ether [bp 40°-60° C.] afforded material of mp 56°-57° C., νmax 3170, 3120, 2230, 1660, 1420, 1355, 1280 cm-1 ; δ(CDCl3) 0.84 (3H, distorted t, terminal CH3), 1.11-1.67 (18H, m, alkylene chain), 2.40 (2H, t, J 6.3 Hz, CH2C≡C), 6.47 (1H, d, J ca 2 Hz, C-4H), 7.51 (1H, d, J ca 2 Hz, C-5H), 9.71 (1H, s CHO).

Sources & evidence

ORD record
ord-07f71a5545ef48b8a54cbf047cdaec4a
Source dataset
uspto-grants-1988_03
Patent number
US04732901

Linked notes

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