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Sodium hydride → (2-Iodo-3-methyl-benzyloxy)-acetic acid tert-butyl ester

HRID 723091
ノート
印刷プレビュー

反応式

HRID 723091 の反応式
[I:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[H-].[Na+].[C:13]([O:17][C:18](=[O:21])[CH2:19]Br)([CH3:16])([CH3:15])[CH3:14]>CN(C=O)C>[C:13]([O:17][C:18](=[O:21])[CH2:19][O:10][CH2:9][C:3]1[CH:4]=[CH:5][CH:6]=[C:7]([CH3:8])[C:2]=1[I:1])([CH3:16])([CH3:15])[CH3:14]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 15717698(2-Iodo-3-methylphenyl)methanol

生成物 1

HCID 69586418(2-Iodo-3-methyl-benzyloxy)-acetic acid tert-butyl ester収率 53%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
0 °C

実験手順

(2-Iodo-3-methyl-phenyl)-methanol (1608 mg, 6.8 mmol, Example 131: step b) was dissolved into DMF (10 mL). The solution was cooled to 0° C. To this was added sodium hydride in one portion and the reaction continued to stir at 0° C. for 30 minutes. To the cooled solution was added t-butylbromoacetate (1.3 mL, 8.9 mmol) and then the reaction was warmed to RT and then heated to 50° C. for 4 hours. The solvents were removed in vacuo and the resulting residue was dissolved into EtOAc and washed with brine. The combined organic layers were dried (MgSO4) and the solvent was removed in vacuo resulting in the title compound (1.29 g, 53%) that was used with out further purification. 1H-NMR (CDCl3): δ 7.28–7.13 (m, 3H), 4.63 (s, 2H), 4.07 (s, 2H), 2.44 (s, 3H), 1.47 (s, 9H).

後処理

  1. temperaturethe reaction was warmed to RT
  2. temperatureheated to 50° C. for 4 hours
  3. customThe solvents were removed in vacuo
  4. dissolutionthe resulting residue was dissolved into EtOAc
  5. washwashed with brine
  6. dry with materialThe combined organic layers were dried (MgSO4)
  7. customthe solvent was removed in vacuo

出典と根拠

ORDレコード
ord-420aa265739449b6b9cce6cd7643230f
出典データセット
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07138530B2

反応ノート

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