Water → 7-(2-cyclopropylethynyl)-3,4-dihydro-2H-1-benzopyran-4-one

HRID 63087노트

반응식

HRID 63087 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:12])[CH2:7][CH2:8][O:9]2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH:20]1([C:23]#[CH:24])[CH2:22][CH2:21]1.O>CN(C=O)C.[Cu]I>[CH:20]1([C:23]#[C:24][C:2]2[CH:3]=[CH:4][C:5]3[C:6](=[O:12])[CH2:7][CH2:8][O:9][C:10]=3[CH:11]=2)[CH2:22][CH2:21]1

참가 물질

7

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 138823CyclopropylacetyleneHCID 223357367-bromo-3,4-dihydro-2H-1-benzopyran-4-one

생성물 1

HCID 867282157-(2-cyclopropylethynyl)-3,4-dihydro-2H-1-benzopyran-4-one수율 88.3%

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

To a solution of 7-bromochroman-4-one (2.0 g, 8.8 mmol) in DMF (10 mL) was added CuI (380 mg, 1.7 mmol), Pd(PPh3)Cl2 (540 mg, 0.8 mmol) and triethylamine (5 mL) under nitrogen at rt. The suspension was warmed to 100° C. and then cyclopropylacetylene (1.1 g, 17.6 mmol) was added dropwise. The mixture was stirred at 100° C. under nitrogen for 2 h. The reaction mixture was cooled to rt, poured into water, and extracted with EtOAc. Organics were separated and washed with brine, dried (Na2SO4), and concentrated. The residue was purified by silica gel chromatography to give 1.65 g (88%) of the title compound as a tan solid. 1H NMR (300 MHz, CDCl3): δ 0.83-0.93 (4H, m), 1.44-1.49 (1H, m), 2.79 (2H, t, J=6.6 Hz), 4.52 (2H, t, J=6.6 Hz), 6.96-7.00 (2H, m), 7.79 (1H, d, J=7.8 Hz). [M+H] calc'd for C14H12O, 213; found 213.

후처리

  1. temperatureThe reaction mixture was cooled to rt
  2. extractionextracted with EtOAc
  3. customOrganics were separated
  4. washwashed with brine
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-92a41fbae0444846a8710469fb61aed5
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09447045B2

반응 노트

불러오는 중…