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Sodium Carbonate → 4-{Cyclooctylidene[4-(3,5-dimethyl-4-isoxazolyl)phenyl]methyl}phenol

HRID 229272
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HRID 229272 반응식
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8](=[C:16]2[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:24][C:25]1[C:29](B(O)O)=[C:28]([CH3:33])[O:27][N:26]=1.C([O-])([O-])=O.[Na+].[Na+]>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1COCC1.O>[C:16]1(=[C:8]([C:5]2[CH:6]=[CH:7][C:2]([C:29]3[C:25]([CH3:24])=[N:26][O:27][C:28]=3[CH3:33])=[CH:3][CH:4]=2)[C:9]2[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][CH:10]=2)[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]1
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반응물 3

HCID 10340Sodium CarbonateHCID 27343463,5-Dimethylisoxazole-4-boronic acidHCID 686544754-[(4-Bromophenyl)(cyclooctylidene)methyl]phenol

생성물 1

HCID 111767004-{Cyclooctylidene[4-(3,5-dimethyl-4-isoxazolyl)phenyl]methyl}phenol수율 77%

시약·촉매·용매 2

HCID 178418476HCID 178418476, 화합물촉매
HCID 21881883Oxolane--water (1/1)용매

실험 절차

The procedure described for 202 was used. A round-bottomed flask was charged with 4-[(4-bromophenyl)(cyclooctylidene)methyl]phenol (49) (0.150 g, 0.404 mmol), PdCl2(PPh3)2, (0.028 g, 0.40 mmol), (3,5-dimethyl-4-isoxazolyl)boronic acid (0.113 g, 0.80 mmol), Na2CO3 (0.086 g, 0.808 mmol), and THF/H2O (4:1, 5 mL). The reaction mixture was refluxed for 10 h. Standard workup and purification by flash silica gel chromatography provided 0.120 g (77%) of the title compound 205 as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 9.27 (s, 1H), 7.30 (d, J=6.00 Hz, 2H), 7.21 (d, J=6.30 Hz, 2H), 6.96 (d, J=6.0 Hz, 2H), 6.69 (d, J=6.0 Hz, 2H), 2.37 (br s, 3H), 2.19 (s, 7H), 2.60 (br s, 2H), 1.50 (br s, 8H). LCMS (ESI): m/z 386 (M−H)−.

후처리

  1. temperatureThe reaction mixture was refluxed for 10 h
  2. customStandard workup and purification by flash silica gel chromatography

출처 및 근거

ORD 기록
ord-f7a2a10a94bc4efe939d21d9703e9bf4
출처 데이터셋
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07560589B2

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