3-Butyn-1-OL → 4-(4-Chloro-2-methoxy-phenyl)-but-3-yn-1-ol

HRID 2383996노트

반응식

HRID 2383996 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[O:9][CH3:10].[CH2:11]([OH:15])[CH2:12][C:13]#[CH:14]>N1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([C:14]#[C:13][CH2:12][CH2:11][OH:15])=[C:3]([O:9][CH3:10])[CH:4]=1

참가 물질

6

반응물 2

HCID 135663-Butyn-1-OLHCID 179848451-Bromo-4-chloro-2-methoxybenzene

생성물 1

HCID 591924974-(4-Chloro-2-methoxy-phenyl)-but-3-yn-1-ol수율 77%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418397HCID 178418397, 화합물촉매HCID 31268Pyrrolidine용매2회

반응 조건

온도
80 °C

실험 절차

To a stirred solution of 2-bromo-5-chloroanisole (2 g, 9 mmol), Pd(PPh3)4 (520 mg, 0.45 mmol), and CuI (400 mg) in pyrrolidine (20 mL) was added a solution of 3-butyn-1-ol (1.26 g, 18 mmol) in pyrrolidine (30 mL). The reaction mixture was stirred at 80° C. for 6 h, and then concentrated in vacuo. The resulting residue was extracted with ethyl acetate and the organic phase was washed with 1N hydrochloric acid, followed by water, then brine, and dried over sodium sulfate. Upon removal of the solvent under reduced pressure, the crude product was subjected to column chromatography on silica gel (gradient elution with 0%-40% EtOAc/hexane) to give 4-(4-chloro-2-methoxy-phenyl)-but-3-yn-1-ol as a colorless oil (1.46 g, 76.7%). 1H NMR (300 MHz, CDCl3) δ ppm 7.29 (d, J=8.2 Hz, 1H), 6.88 (dd, J=8.2, 1.6 Hz, 1H), 6.85 (d, J=1.6 Hz, 1H), 3.87 (s, 3H), 3.82 (t, J=6.2 Hz, 2H), 2.73 (t, J=6.2 Hz, 2H), 1.92 (br. s, 1H).

후처리

  1. concentrationconcentrated in vacuo
  2. extractionThe resulting residue was extracted with ethyl acetate
  3. washthe organic phase was washed with 1N hydrochloric acid
  4. dry with materialbrine, and dried over sodium sulfate
  5. customUpon removal of the solvent under reduced pressure

출처 및 근거

ORD 기록
ord-8f7255a983da46bb96a281ca02e96eee
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08263656B2

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