Acetonitrile → 3,4-Bis-(1,1-dimethyl-prop-2-ynyloxy)-xanthen-9-one

HRID 734184노트

반응식

HRID 734184 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[C:15]=1[OH:16])=[CH:11][CH:10]=[CH:9][CH:8]=3.Cl[C:19]([CH3:23])([CH3:22])[C:20]#[CH:21].N12CCCN=[C:30]1[CH2:29][CH2:28][CH2:27]CC2.[C:35](#N)C>>[CH3:22][C:19]([CH3:23])([O:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:17])[C:7]3[C:12]([O:13][C:14]=2[C:15]=1[O:16][C:29]([CH3:30])([CH3:35])[C:28]#[CH:27])=[CH:11][CH:10]=[CH:9][CH:8]=3)[C:20]#[CH:21]

참가 물질

5

반응물 4

HCID 6342AcetonitrileHCID 706791-Butyne, 3-chloro-3-methyl-HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 57483823,4-Dihydroxy-xanthone

생성물 1

HCID 593560783,4-Bis-(1,1-dimethyl-prop-2-ynyloxy)-xanthen-9-one수율 25%

반응 조건

온도
75 °C

실험 절차

A solution of 3,4-dihydroxy-xanthen-9-one (1.25 g, 5.47 mmol), cupric chloride (30.2 mg, 0.225), 3-chloro-3-methyl-1-butyne (3.36 mL, 29.9 mmol), 1,8-diazabicyclo[5.4.0]undec-7-ene (2.00 mL, 13.3 mmol), and acetonitrile (100 mL) was stirred at room temperature for 11 h under argon. The solution was then heated at 75° C. for 2 h and cooled to room temperature. The solution was partitioned between ethyl acetate (100 mL) and water (75 mL). The ethyl acetate layer was dried over sodium sulfate and was concentrated by rotary evaporation. The product was purified by flash column chromatography (10:1 hexanes/ethyl acetate) to yield 496 mg (25%) of the title compound as a light yellow solid. 1H NMR (CDCl3, 300 MHz): δ 8.33 (dd, J1=7.97 Hz, J2=1.65, 1H), 8.07 (d, J=9.06 Hz, 1H), 7.71 (ddd, J1=8.18 Hz, J2=7.08, J3=1.58, 1H), 7.65 (d, J=9.06 Hz, 1H), 7.52 (dd, J1=8.52 Hz, J2=0.55, 1H), 7.38 (m, 1H), 2.66 (s, 1H), 2.30 (s, 1H), 1.84 (s, 6H), 1.77 (s, 6H).

후처리

  1. temperaturecooled to room temperature
  2. customThe solution was partitioned between ethyl acetate (100 mL) and water (75 mL)
  3. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  4. concentrationwas concentrated by rotary evaporation
  5. customThe product was purified by flash column chromatography (10:1 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-d7f4fc90fad34e528c2636322cc83446
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07592143B2

반응 노트

불러오는 중…