4-Bromoanisole → HCID 11381397, 화합물

HRID 1950604노트

반응식

HRID 1950604 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[C:9](=[O:15])[CH2:8][CH2:7][CH2:6]2.Br[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1.CC(C)([O-])C.[Na+]>O1CCCC1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[C:11]([O:13][CH3:14])[CH:12]=1)[C:9](=[O:15])[CH:8]([C:17]1[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=1)[CH2:7][CH2:6]2

참가 물질

6

반응물 3

HCID 77304-BromoanisoleHCID 114470756,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-oneHCID 23676156Sodium t-butoxide

생성물 1

HCID 11381397HCID 11381397, 화합물수율 78.8%

시약·촉매·용매 2

HCID 634876Binap, (A+-)-촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
75 °C

실험 절차

The title compound was synthesized by referring to J. Am. Chem. Soc., 1997, 119 (45), 11108. To a solution of 6,8-dimethoxy-3,4-dihydro-2H-naphthalen-1-one (11.9 g) in tetrahydrofuran (200 ml) were sequentially added 4-bromoanisole (16.2 g), sodium tert-butoxide (11.1 g), (±)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (1.3 g) and tris(dibenzylidene)acetone dipalladium(0) (792 mg), and the solution was stirred for 1.5 hours at 75° C. under a nitrogen atmosphere. The solution was extracted with ethyl acetate, then sequentially washed with water and brine, dried over anhydrous magnesium sulfate, then the solvent was evaporated in vacuo; the resulting crude crystal was suspended in diethyl ether and then filtered. The mother liquor was concentrated in vacuo, the resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate system); the resulting crystal was suspended in diethyl ether, then filtered, and combined to provide the title compound (14.2 g).

후처리

  1. customThe title compound was synthesized
  2. extractionThe solution was extracted with ethyl acetate
  3. washsequentially washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was evaporated in vacuo
  6. filtrationfiltered
  7. concentrationThe mother liquor was concentrated in vacuo
  8. customthe resulting residue was purified by silica gel column chromatography (hexane-ethyl acetate system)
  9. filtrationfiltered

출처 및 근거

ORD 기록
ord-2bc212f8fbfa43b8b2944f855c37f0d3
출처 데이터셋
uspto-grants-2013_03
특허 번호
US08399520B2

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