Sodium Iodide → 3-[2-[2-(2-Ethoxyethoxy)ethoxy]ethoxy]-5-(octadecyloxy)benzoic acid phenylmethyl ester

HRID 488276ノート

反応式

HRID 488276 の反応式
[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([OH:35])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH2:37]([O:39][CH2:40][CH2:41][O:42][CH2:43][CH2:44][O:45][CH2:46][CH2:47]Br)[CH3:38].[I-].[Na+].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CN(C=O)C>[C:1]1([CH2:7][O:8][C:9](=[O:36])[C:10]2[CH:15]=[C:14]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH3:34])[CH:13]=[C:12]([O:35][CH2:47][CH2:46][O:45][CH2:44][CH2:43][O:42][CH2:41][CH2:40][O:39][CH2:37][CH3:38])[CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

7

反応物 4

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 147041761-Bromo-2-(2-(2-ethoxyethoxy)ethoxy)ethaneHCID 152334763-Hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester

生成物 1

HCID 537975283-[2-[2-(2-Ethoxyethoxy)ethoxy]ethoxy]-5-(octadecyloxy)benzoic acid phenylmethyl ester収率 67%

試薬・触媒・溶媒 2

HCID 180Acetone溶媒HCID 6228Dimethylformamide溶媒

実験手順

A mixture of 2 g (4 mmol) of 3-hydroxy-5-(octadecyloxy)benzoic acid phenylmethyl ester, 3.65 g (15.8 mmol) of 2-[2-(2-ethoxyethoxy)ethoxy]ethyl bromide, 1.2 g (8 mmol) of sodium iodide and 2.2 g (16 mmol) of potassium carbonate in 60 ml of acetone and 30 ml of DMF was stirred at reflux for 40 hours. The usual workup followed by chromatography of the crude product on 200 g of silica gel using 40% ethyl acetate-hexane gave 1.76 g of 3-[2-[2-(2-ethoxyethoxy)ethoxy]ethoxy]-5-(octadecyloxy)benzoic acid phenylmethyl ester as an oil. The nmr and mass spectra were compatible with the structure.

後処理

  1. temperatureat reflux for 40 hours

出典と根拠

ORDレコード
ord-cb56a5f6c8d84f578e9e332ee1b8b605
出典データセット
uspto-grants-1994_03
特許番号
US05298652

反応ノート

読み込み中…