Hydrochloric Acid → 2-Methyl-1-benzothiophene-3-carbaldehyde

HRID 225904

反応式

HRID 225904 の反応式
Cl[Sn](Cl)(Cl)Cl.[CH3:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[CH:8]=1.[CH3:16][O:17]C(Cl)Cl.Cl>C(Cl)Cl>[CH3:6][C:7]1[S:11][C:10]2[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=2[C:8]=1[CH:16]=[O:17]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 21004Methane, dichloromethoxy-HCID 24287Tin tetrachlorideHCID 709522-Methylbenzo(b)thiophene

生成物 1

HCID 37754672-Methyl-1-benzothiophene-3-carbaldehyde収率 98.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

SnCl4 (20 mL, 67 mmole) was added over 5 min to a stirred solution of 2-methylbenzo[b]thiophene (5.0 g, 33.7 mmole) in CH2Cl2 (75 mL) at 0° C. under argon. After 15 minutes, dichloromethyl methyl ether (3.7 mL, 41 mmole) was added. The reaction became a yellowish colored suspension. The reaction was allowed to warm to RT and stirred for 16 h, then was poured onto ice water (200 mL). The aqueous mixture was acidified with 1.0 N HCl (100 mL) and stirred until the suspension dissolved. The organic phase was separated, dried (MgSO4), and concentrated under vacuum. Purification by flash chromatography on silica gel (10% ethyl acetate/hexane) gave the tide compound (5.83 g, 98%) as a white crystalline solid: 1H NMR (400 MHz, CDCl3) δ 10.38 (s, 1 H), 8.61 (d, J=8.1 Hz, 1 H), 7.77 (d, J=8.0 Hz, 1 H), 7.48 (t, 1 H), 7.39 (t, 1 H), 2.93 (s, 3 H).

後処理

  1. additionwas poured onto ice water (200 mL)
  2. stirringstirred until the suspension
  3. dissolutiondissolved
  4. customThe organic phase was separated
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under vacuum
  7. customPurification by flash chromatography on silica gel (10% ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-dd370399441640d0bfbc366c5f2e8f00
出典データセット
uspto-grants-2009_07
特許番号
US07557125B2

関連ノート

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