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

HRID 255994

反応式

HRID 255994 の反応式
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1Br)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[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]>>[C:20]([C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[CH2:11][CH:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:4]([O:3][CH2:1][CH3:2])=[O:19])#[C:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH3:32]

参加物

3

反応物 2

HCID 1177541-TridecyneHCID 12853296Diethyl 2-(2-bromobenzyl)malonate

生成物 1

HCID 20165388Diethyl 2-[2-(1-tridecynyl)phenyl]methylpropan-1,3-dioate収率 30.3%

実験手順

Reaction of diethyl(2-bromobenzyl)propan-1,3-dioate (11.87 g, 30 mmol) with 1-tridecyne (11.10 g, 45 mmol) as described in example 3 gave 3.89 g (29%) of the title compound as a pale yellow oil after chromatography. It had νmax (film) 1735, 1755, 2840, 2920 cm-1 ; δ(CDCl3) 0.87 (3H, distorted t, terminal CH3), 1.08 (6H, t, J 7 Hz, ester CH3), 1.28 (18H, m, alkylene chain), 2.42 (2H, t, J 6 Hz, C≡C--CH2), 3.31 (2H, d, J 7.5 Hz, ArCH2), 3.90 (1H, t, J 7.5 Hz, methine H), 4.12 (4H, q, J 7.5 Hz, ester CH2), 7.15 (3H, m, aromatics), 7.36 (1H, m, aromatic). M+ 428.2928 (C27H40O4 requires; 428.2926).

出典と根拠

ORDレコード
ord-bb4da2c74b46483b9aa5adca68a6d049
出典データセット
uspto-grants-1987_10
特許番号
US04699995

関連ノート

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