Tributylphosphine → 7-[(1-{4-[(4-butylphenyl)ethynyl]phenyl}pentyl)oxy]-2,2-dimethyl-4H-1,3-benzodioxin-4-one

HRID 551913노트

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HRID 551913 반응식
[OH:1][C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[O:11])[O:9][C:8]([CH3:13])([CH3:12])[O:7][C:6]=2[CH:14]=1.C(P(CCCC)CCCC)CCC.[CH2:28]([C:32]1[CH:37]=[CH:36][C:35]([C:38]#[C:39][C:40]2[CH:45]=[CH:44][C:43]([CH:46](O)[CH2:47][CH2:48][CH2:49][CH3:50])=[CH:42][CH:41]=2)=[CH:34][CH:33]=1)[CH2:29][CH2:30][CH3:31]>C1(C)C=CC=CC=1>[CH2:28]([C:32]1[CH:37]=[CH:36][C:35]([C:38]#[C:39][C:40]2[CH:45]=[CH:44][C:43]([CH:46]([O:1][C:2]3[CH:3]=[CH:4][C:5]4[C:10](=[O:11])[O:9][C:8]([CH3:12])([CH3:13])[O:7][C:6]=4[CH:14]=3)[CH2:47][CH2:48][CH2:49][CH3:50])=[CH:42][CH:41]=2)=[CH:34][CH:33]=1)[CH2:29][CH2:30][CH3:31]

참가 물질

5

반응물 3

HCID 13831TributylphosphineHCID 105839507-hydroxy-2,2-dimethyl-4H-benzo[d][1,3]dioxin-4-oneHCID 575545631-{4-[(4-Butylphenyl)ethynyl]phenyl}-1-pentanol

생성물 1

HCID 575545257-[(1-{4-[(4-butylphenyl)ethynyl]phenyl}pentyl)oxy]-2,2-dimethyl-4H-1,3-benzodioxin-4-one수율 64%

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
0 °C

실험 절차

A solution of 7-hydroxy-2,2-dimethyl-4H-1,3-benzodioxin-4-one (363 mg, 1.87 mmol, described in J. Chem. Soc., Perkin Trans. 1, 2000, 4265-4278) and tri-n-butylphosphine (378 mg, 1.87 mmol) in anhydrous toluene (10 mL) was chilled at 0° C. To this solution was added N,N,N′,N′-tetramiethylazodicarboxamide (322 mg, 1.87 mmol) at once and the resulting reaction mixture was stirred 10 min at 0° C. Then 1-{4-[(4-butylphenyl)ethynyl]phenyl}-1-pentanol (461.5 mg; 1.44 mmol; 1.0 eq.) was added and the resulting mixture was stirred overnight at rt. The solvent was removed under reduced pressure and the crude mixture was purified by chromatography on silicagel (EtOAc/c-Hex (1/9)) to give 456 mg (64%) of the title compound. HPLC, Rt: 6.2 min (purity: 97.0%). 1H NMR (CDCl3) δ 7.78 (d, J=8.7 Hz, 1H), 7.50 (d, J=8.3 Hz, 2H), 7.42 (d, J=8.2 Hz, 2H), 7.29 (d, J=8.3 Hz, 2H), 7.15 (d, J=8.3 Hz, 2H), 6.61 (dd, J=2.4 Hz, J=9.0 Hz, 1H), 6.29 (d, J=2.3 Hz, 1H), 5.16-5.07 (m, 1H), 2.61 (t, J=7.8 Hz, 2H), 2.08-1.93 (m, 1H), 1.91-1.75 (m, 1H), 1.73-1.24 (m, 14H), 0.98-0.84 (m, 6H).

후처리

  1. additionTo this solution was added N,N,N′,N′-tetramiethylazodicarboxamide (322 mg, 1.87 mmol) at once and
  2. customthe resulting reaction mixture
  3. stirringthe resulting mixture was stirred overnight at rt
  4. customThe solvent was removed under reduced pressure
  5. customthe crude mixture was purified by chromatography on silicagel (EtOAc/c-Hex (1/9))

출처 및 근거

ORD 기록
ord-630d8e51cd1e4d09aa7183f29efb5e8d
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947851B2

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