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

HRID 1825950

반응식

HRID 1825950 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 37754672-Methyl-1-benzothiophene-3-carbaldehyde수율 98.2%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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 title 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=8.0Hz, 1 H), 7.48 (t, 1 H), 7.39 (t, 1 H), 2.93 (s, 3 H).

후처리

  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)

출처 및 근거

ORD 기록
ord-ade0b79cad8c4592962ef6e40e3a0abe
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07049310B2

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