Water → Methyl 3-methoxy4-(5-nitrobenzo[b]thien-3-ylmethyl)benzoate

HRID 1080776

反応式

HRID 1080776 の反応式
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]2[S:8][CH:9]=[CH:10][C:6]=2[CH:5]=1)([O-:3])=[O:2].Br[CH2:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[O:25][CH3:26].O>ClCCl>[CH3:26][O:25][C:16]1[CH:17]=[C:18]([CH:23]=[CH:24][C:15]=1[CH2:14][C:10]1[C:6]2[CH:5]=[C:4]([N+:1]([O-:3])=[O:2])[CH:12]=[CH:11][C:7]=2[S:8][CH:9]=1)[C:19]([O:21][CH3:22])=[O:20]

参加物

5

反応物 3

HCID 962WaterHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 124140845-Nitro-1-benzothiophene

生成物 1

HCID 14763112Methyl 3-methoxy4-(5-nitrobenzo[b]thien-3-ylmethyl)benzoate

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

Stannic chloride (0.41 g.) was added to a stirred solution of 5-nitrobenzo[b]thiophene (0.28 g.) and methyl 4-bromomethyl-3-methoxybenzoate (B) (0.61 g.) in dichloromethane (5 ml.). The mixture was heated under reflux for 18 hours. The cooled mixture was poured into water (10 ml.) and extracted with dichloromethane (2×20 ml.). The combined extracts were dried (MgSO4) and evaporated. The oil was purified by flash chromatography on silica gel (100 ml.) eluting with 1:9 v/v ethyl acetate:hexane. The solid obtained was crystallized from hexane to give methyl 3-methoxy-4-(5-nitrobenzo[b]thien-3-ylmethyl)benzoate (I) as a solid (0.16 g., 30%); NMR: (250 MHz, CDCl3): 3.92(s, 3H, OCH3), 3.98(s,3H, OCH3), 4.28(s,2H, CH2 --Ar), 7.15 (d,1H), 7.22(s,1H), 7.56(m,2H), 7.93(d,1H), 8.19(dd, 1H); 8.73(d,1H).

後処理

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 18 hours
  3. extractionextracted with dichloromethane (2×20 ml.)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. customevaporated
  6. customThe oil was purified by flash chromatography on silica gel (100 ml.)
  7. washeluting with 1:9 v/v ethyl acetate
  8. customThe solid obtained
  9. customwas crystallized from hexane

出典と根拠

ORDレコード
ord-2bc36345b6684ca1842f473286c5f136
出典データセット
uspto-grants-1996_12
特許番号
US05583152

関連ノート

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