Diethyl Ether → Benzofuran-5-yl(phenyl)methanol

HRID 2075191

반응식

HRID 2075191 반응식
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=[O:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1.[C:12]1([Mg]Br)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(OCC)C>C1COCC1>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[OH:11])=[CH:9][C:4]=2[CH:3]=[CH:2]1

참가 물질

5

반응물 3

HCID 3283Diethyl EtherHCID 27738751-Benzofuran-5-carbaldehydeHCID 178418255HCID 178418255, 화합물

생성물 1

HCID 58415371Benzofuran-5-yl(phenyl)methanol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 1-benzofuran-5-carbaldehyde (2.70 g, 18.5 mmol) in 50 mL THF under N2 was added phenylmagnesium bromide 3.0M solution in diethyl ether (7.39 mL, 22.2 mmol). The reaction was allowed to stir for 1 h, then was quenched with NH4Cl sat'd aq., extracted with diethyl ether, washed with brine, dried over anhyd. sodium sulfate, filtered, and concentrated in vacuo to a solid to give benzofuran-5-yl(phenyl)methanol which was used without further purification. 1H NMR (400 MHz, DMSO-d6) δ ppm 7.94 (d, J=2.0 Hz, 1H), δ 7.64 (s, 1H), 7.49 (d, J=8.5 Hz, 1H), 7.36-7.42 (m, 2H), 7.26-7.33 (m, 3H), 7.19 (t, J=7.3 Hz, 1H), 6.92 (d, J=1.5 Hz, 1H), 5.88 (d, J=4.0 Hz, 1H), 5.77-5.83 (m, 1H).

후처리

  1. customwas quenched with NH4Cl sat'd aq.
  2. extractionextracted with diethyl ether
  3. washwashed with brine
  4. customdried over anhyd
  5. filtrationsodium sulfate, filtered
  6. concentrationconcentrated in vacuo to a solid

출처 및 근거

ORD 기록
ord-2bb8768110694cde84453063495b7b0f
출처 데이터셋
uspto-grants-2011_04
특허 번호
US07919519B2

연결된 노트

불러오는 중…