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Water → HCID 57750763, 화합물

HRID 900996
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HRID 900996 반응식
[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10]OC)[CH:9]=1.B(Cl)(Cl)[Cl:15].O>ClCCl>[CH3:1][O:2][C:3](=[O:13])[CH2:4][C:5]1[S:6][CH:7]=[C:8]([CH2:10][Cl:15])[CH:9]=1
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참가 물질

5

반응물 3

HCID 962WaterHCID 25135Boron TrichlorideHCID 57750764HCID 57750764, 화합물

생성물 1

HCID 57750763HCID 57750763, 화합물수율 81%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of (4-methoxymethyl-thiophen-2-yl)-acetic acid methyl ester (0.70 g, 3.50 mmol) in dichloromethane (20 mL) is treated with boron trichloride (3.50 mL, 1.0 M, 3.50 mmol) in a dropwise maner. After stirring at room temperature for 30 min the mixture is poured into water and extracted with dichloromethane (3×). The combined organic layers are washed with saturated aq NaCl, dried over Na2SO4, filtered and concentrated in vacuo. The resulting residue is purified by chromatography (silica gel, 5-10% ethyl acetate in heptane) to give (4-chloromethyl-thiophen-2-yl)-acetic acid methyl ester (0.58 g, 81%) as a colorless oil: 1H NMR (CDCl3, 300 MHz) δ 7.18 (s, 1 H), 6.95 (s, 1 H), 4.52 (s, 2 H), 3.80 (s, 2 H), 3.72 (s, 3 H).

후처리

  1. extractionextracted with dichloromethane (3×)
  2. washThe combined organic layers are washed with saturated aq NaCl
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue is purified by chromatography (silica gel, 5-10% ethyl acetate in heptane)

출처 및 근거

ORD 기록
ord-f23a41db597d4b869f5591d206efbe96
출처 데이터셋
uspto-grants-2008_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07361671B2

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