2-Bromo-naphtho[2,3-b]furan-4,9-dione → 2-Methylthio-naphtho[2,3-b]furan-4,9-dione

HRID 540652ノート

反応式

HRID 540652 の反応式
Br[C:2]1[O:6][C:5]2[C:7](=[O:16])[C:8]3[C:13]([C:14](=[O:15])[C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.C(S)[CH2:18][S:19]([O-])(=O)=O.[Na+]>O1CCCC1.O>[CH3:18][S:19][C:2]1[O:6][C:5]2[C:7](=[O:16])[C:8]3[C:13]([C:14](=[O:15])[C:4]=2[CH:3]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3

参加物

5

反応物 2

HCID 3962872-Bromo-naphtho[2,3-b]furan-4,9-dioneHCID 23662354Mesna

生成物 1

HCID 107766732-Methylthio-naphtho[2,3-b]furan-4,9-dione収率 90.1%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To the solution of 0.7 gram (2.5 mmoles) of 2-bromo-naphtho[2,3-b]furan-4,9-dione in 20 mL of tetrahydrofuran at room temperature, 0.4 grams (5.0 mmoles) of MeSNa in 5 mL of water was added dropwise over 1 minute. The mixture was further stirred for 2 hours at room temperature, and then evaporated to remove tetrahydrofuran. To the residue, 20 mL of 1N hydrochloric acid was added, and the resulting mixture was filtered. The solid was washed with water, and then crystallized in ethanol/water. Pure crystal product was filtered and dried under vacuum. 0.55 grams of product (yield 90%) was obtained and characterized by 1H NMR and mass spectrum. 1H NMR (in CDCl3) δ 2.66 (s, 3H), 6.79 (s, 1H), 7.75-7.79 (m, 2H), 8.18-8.25 (m, 2H). Mass (M+H) is 245.

後処理

  1. customevaporated
  2. customto remove tetrahydrofuran
  3. additionTo the residue, 20 mL of 1N hydrochloric acid was added
  4. filtrationthe resulting mixture was filtered
  5. washThe solid was washed with water
  6. customcrystallized in ethanol/water
  7. filtrationPure crystal product was filtered
  8. customdried under vacuum

出典と根拠

ORDレコード
ord-ced5cc5c55bd4c3b8a67026cd95b98e1
出典データセット
uspto-grants-2014_10
特許番号
US08871802B2

反応ノート

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