Sodium hydride → O-(2-methoxybenzyl)-6-dimethylaminohexanol

HRID 272798

反応式

HRID 272798 の反応式
[CH3:1][N:2]([CH3:10])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][OH:9].[H-].[Na+].[CH3:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17]Cl>C1COCC1.CN(C=O)C>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[CH2:17][O:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:10])[CH3:1]

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 746236-Dimethylaminohexan-1-olHCID 814952-(Chloromethyl)anisole

生成物 1

HCID 23436782O-(2-methoxybenzyl)-6-dimethylaminohexanol収率 97%

試薬・触媒・溶媒 1

HCID 21974620tetrahydrofuran N,N-dimethylformamide溶媒

実験手順

6-Dimethylamino-1-hexanol (8.80 g, 60.6 mmol) was dissolved in 2/1 mixture of THF/DMF (150 mL) and the solution was cooled in an ice/water bath. Sodium hydride (3.25 g, 80.8 mmol, 60% in oil) was added. After 40 min., 2-methoxybenzyl chloride (6.28 g, 40.4 mmol) was added and the solution was allowed to warm to room temperature over 1 h. After 3 h, the reaction was quenched by the addition of 1M NaHSO4. Tetrahydrofuran was removed in vacuo, and the solution was washed with EtOAc. The aqueous phase was basified with 3M NaOH and extracted with ether. The combined ether phases were dried over K2CO3, filtered, and the product was crystallized by the addition of 4M HCl/dioxane to give O-(2-methoxybenzyl)-6-dimethylaminohexanol (10.4 g) as a white solid.

後処理

  1. temperaturethe solution was cooled in an ice/water bath
  2. waitAfter 3 h
  3. customthe reaction was quenched by the addition of 1M NaHSO4
  4. customTetrahydrofuran was removed in vacuo
  5. washthe solution was washed with EtOAc
  6. extractionextracted with ether
  7. dry with materialThe combined ether phases were dried over K2CO3
  8. filtrationfiltered
  9. customthe product was crystallized by the addition of 4M HCl/dioxane

出典と根拠

ORDレコード
ord-ca56edcdec714e2ab933b664cdae51ed
出典データセット
uspto-grants-2008_11
特許番号
US07456203B2

関連ノート

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