Ethyl Bromide → Sodium

HRID 619780노트

반응식

HRID 619780 반응식
[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]

참가 물질

7

반응물 4

HCID 6332Ethyl BromideHCID 70897-Hydroxy-2-naphthalenesulfonic acidHCID 24758Sodium hydride2회HCID 5360545Sodium

생성물 2

HCID 5360545SodiumHCID 218459087-Ethoxynaphthalene-2-sulfonic acid

시약·촉매·용매 1

HCID 6228Dimethylformamide용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ae063843e95b4d9b8284c38dd13ef153
출처 데이터셋
uspto-grants-1999_09
특허 번호
US05958918

반응 노트

불러오는 중…