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Triphenylphosphine → Ethyl [(4-{[1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethyl]oxy}-2-methylphenyl)oxy]acetate

HRID 1391773
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HRID 1391773 반응식
CC(OC(/N=N/C(OC(C)C)=O)=O)C.[OH:15][C:16]1[CH:28]=[CH:27][C:19]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:18]([CH3:29])[CH:17]=1.[Br:30][C:31]1[N:36]=[C:35]([CH:37](O)[CH2:38][O:39][CH2:40][CH3:41])[CH:34]=[CH:33][CH:32]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[Br:30][C:31]1[N:36]=[C:35]([CH:37]([O:15][C:16]2[CH:28]=[CH:27][C:19]([O:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:18]([CH3:29])[CH:17]=2)[CH2:38][O:39][CH2:40][CH3:41])[CH:34]=[CH:33][CH:32]=1
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참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 21986458Ethyl (4-hydroxy-2-methylphenoxy)acetateHCID 586298281-(6-Bromo-2-pyridinyl)-2-(ethyloxy)ethanol

생성물 1

HCID 58629848Ethyl [(4-{[1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethyl]oxy}-2-methylphenyl)oxy]acetate수율 63.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of diisopropylazodicarboxylate (0.96 mL, 4.89 mmol) in dry THF (35 mL) was added drop-wise, under nitrogen, over 2 h (using a syringe pump) to a solution of ethyl (4-hydroxy-2-methylphenoxy)acetate (735 mg, 3.50 mmol), 1-(6-bromo-2-pyridinyl)-2-(ethyloxy)ethanol (860 mg, 3.49 mmol) and triphenylphosphine (1.28 g, 4.88 mmol) in dry THF (35 mL) at 0° C. The resulting mixture was stirred under nitrogen and gradually allowed to warm to room temperature over 21 h. The solvent was then removed in vacuo and the residue purified by SPE (silica, 2×50 g cartridge), eluting with cyclohexane:EtOAc (gradient 20:1 to 1:1) to afford the title compound as an oil (966 mg).

후처리

  1. customThe solvent was then removed in vacuo
  2. customthe residue purified by SPE (silica, 2×50 g cartridge)
  3. washeluting with cyclohexane

출처 및 근거

ORD 기록
ord-d4c7e9cc36454a4bb05d83544fff421b
출처 데이터셋
uspto-grants-2008_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07338960B2

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