1-Tridecyne → Diethyl 2-[(1-tridecynyl)phenyl]methylenepropan-1,3-dioate

HRID 255991

Reaction equation

HRID 255991 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11].[CH:20]#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]>ClCCl>[C:20]([C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH:8]=[C:9]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:10]([O:12][CH2:13][CH3:14])=[O:11])#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

Participants

4

Reactant 2

HCID 1177541-TridecyneHCID 246693Diethyl [(2-bromophenyl)methylidene]propanedioate

Product 1

HCID 20165387Diethyl 2-[(1-tridecynyl)phenyl]methylenepropan-1,3-dioateYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Reaction of diethyl 2-(2-bromophenyl)methylenepropan-1,3-dioate (6.54 g, 20 mmole, from example 1) with 1-tridecyne (6.1 g, 34 mmole) as described in example 3 gave 5.37 g (63%) of the title compound after chromatography on silica gel eluting with dichloromethane: petroleum ether [bp 60°-80° C.] (1:1). It had, νmax (film) 1730, 2850, 2920 cm-1, δ(CDCl3) 0.84 (3H, distorted t, terminal CH3), 1.13-1.68 (24H, m, ester CH3 +alkylene chain), 2.42 (2H, t, J 6.3 Hz, ≡--CH2), 4.23 (2H, q, J 7.5 Hz, ester CH2), 4.26 (2H, q, J 7.5 Hz, ester CH2), 7.31 (4H, m, aromatics), 8.20 (1H, s, CHO), M+ 426.2780 (C27H38O 4 requires; 426.2770).

Sources & evidence

ORD record
ord-3bf5bdece2bf416db8ec55e2bb72c04f
Source dataset
uspto-grants-1987_10
Patent number
US04699995

Linked notes

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