Ethyl Bromide → Sodium

HRID 619780ノート

反応式

HRID 619780 の反応式
[H-].[Na+].[OH:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([S:14]([OH:17])(=[O:16])=[O:15])=[CH:11]2)=[CH:6][CH:5]=1.[Na:18].Br[CH2:20][CH3:21]>CN(C=O)C>[CH2:20]([O:3][C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[CH:9][C:10]([S:14]([OH:17])(=[O:15])=[O:16])=[CH:11]2)=[CH:6][CH:5]=1)[CH3:21].[Na:18]

参加物

7

反応物 4

HCID 6332Ethyl BromideHCID 70897-Hydroxy-2-naphthalenesulfonic acidHCID 24758Sodium hydride2 回HCID 5360545Sodium

生成物 2

HCID 5360545SodiumHCID 218459087-Ethoxynaphthalene-2-sulfonic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

A 60% dispersion of sodium hydride (0.74 g, 18.45 mmol) in mineral oil is washed with hexanes twice and suspended in 35 mL of DMF. To this mixture is added slowly via an addition funnel 7-hydroxynaphthalene-2-sulfonic acid, sodium salt (2.5 g, 10.1 mmol) in 50 mL of DMF at room temperature. The reaction mixture is stirred for 75 min during which time mild bubbling is observed (H2 evolution). The mixture is treated with bromoethane (2.42 mL, 32.5 mmol) and stirred for 16 hours at room temperature. A little ice is added to decompose the excess NaH and the resultant mixture is concentrated in vacuo. The residue is suspended in acetone and concentrated in vacuo two times and then is dried under high vacuum. The solid is suspended in acetone, filtered and dried to yield the crude 7-ethoxynaphthalene-2-sulfonic acid, sodium salt as a beige solid. A mixture of the sulfonic acid, sodium salt (3.77 g) in 10 mL of thionyl chloride is heated at 80° C. for 2 hours. The mixture is allowed to cool to room temperature and concentrated in vacuo. The residue is diluted in EtOAc and washed successively with water (2×), saturated NaHCO3 solution and saturated NaCl. The organic layer is dried over anhydrous MgSO4, filtered and concentrated to yield 2.65 g of a crude brown oil. The crude product is purified by column chromatography in a gradient of 10% EtOAc/hexanes to 20% EtOAc/hexanes to afford the title compound (1.67 g, 6.17 mmol) as a pale yellow solid.

後処理

  1. custommild bubbling
  2. stirringstirred for 16 hours at room temperature
  3. concentrationthe resultant mixture is concentrated in vacuo
  4. concentrationconcentrated in vacuo two times
  5. customis dried under high vacuum
  6. filtrationfiltered
  7. customdried

出典と根拠

ORDレコード
ord-ae063843e95b4d9b8284c38dd13ef153
出典データセット
uspto-grants-1999_09
特許番号
US05958918

反応ノート

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