2-Bromoethanol → [4-(2-Hydroxyethoxy)-2-methoxybenzyl]carbamic acid tert-butyl ester

HRID 2353602ノート

反応式

HRID 2353602 の反応式
[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2].Br[CH2:20][CH2:21][OH:22]>CC(O)C.[OH-].[Na+]>[C:1]([O:5][C:6](=[O:18])[NH:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:20][CH2:21][OH:22])=[CH:11][C:10]=1[O:16][CH3:17])([CH3:4])([CH3:3])[CH3:2]

参加物

5

反応物 2

HCID 108982-BromoethanolHCID 68450274(4-Hydroxy-2-methoxybenzyl)carbamic acid tert-butyl ester

生成物 1

HCID 68452888[4-(2-Hydroxyethoxy)-2-methoxybenzyl]carbamic acid tert-butyl ester収率 38.5%

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 14798Sodium Hydroxide溶媒

反応条件

温度
85 °C

実験手順

To a stirred solution of (4-hydroxy-2-methoxy-benzyl)-carbamic acid tert-butyl ester (22.8 mg, 0.09 mmol) in 2-propanol (1 mL) and 2 N aq. NaOH (0.15 mL) is added 2-bromoethanol (22.5 mg, 0.18 mmol). The reaction mixture is heated to 85° C. and stirred for 8 h. The mixture is cooled to rt and subjected to prep. HPLC purification to give [4-(2-hydroxy-ethoxy)-2-methoxy-benzyl]-carbamic acid tert-butyl ester (10.3 mg) as a colourless oil. LC-MS: tR=0.85 min, [M+1]+=298.07.

後処理

  1. temperatureThe mixture is cooled to rt
  2. customHPLC purification

出典と根拠

ORDレコード
ord-537e4b15fac44273bfa34e41ed9d749c
出典データセット
uspto-grants-2010_07
特許番号
US07750040B2

反応ノート

読み込み中…