Triphenylphosphine → 2-Bromo-4-methyl-1-((3-methylpent-4-en-2-yl)oxy)benzene

HRID 1400757노트

반응식

HRID 1400757 반응식
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[CH3:10][CH:11]([CH:15]=[CH2:16])[CH:12](O)[CH3:13].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1.O>[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[O:9][CH:15]([CH:11]([CH3:10])[CH:12]=[CH2:13])[CH3:16]

참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 231092-Bromo-4-methylphenolHCID 5447013-Methyl-4-penten-2-olHCID 5462977Diethyl azodicarboxylate

생성물 1

HCID 867108152-Bromo-4-methyl-1-((3-methylpent-4-en-2-yl)oxy)benzene수율 59.8%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2-bromo-4-methylphenol (1 g, 5.35 mmol) and 3-methylpent-4-en-2-ol (2.68 g, 26.7 mmol) in THF (20 mL) was added Ph3P (7.01 g, 26.7 mmol) followed by DEAD (4.23 mL, 26.7 mmol) and the resulting mixture was stirred at room temp for 16 h. Water was then added and the mixture was extracted with ether (2×50 mL), dried (Na2SO4), filtered and concentrated. The residue was then purified by Biotage (0-20% EtOAc/hexane) to afford 2-bromo-4-methyl-1-((3-methylpent-4-en-2-yl)oxy)benzene (860 mg, 3.19 mmol, 59.8% yield) as yellow oil. Product is approx 2:1 mixture of trans/cis isomers. 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=2.0 Hz, 1H), 7.08-7.01 (m, 1H), 6.83-6.79 (m, 1H), 6.02-5.89 (m, 1H), 5.16 (q, J=1.8 Hz, 0.5H), 5.14-5.08 (m, 1.5H), 4.31-4.37 (m, 0.3H), 4.28-4.19 (m, 0.7H), 2.64-2.50 (m, 1H), 2.29 (s, 3H), 1.30-1.24 (m, 3H), 1.19-1.14 (m, 3H).

후처리

  1. extractionthe mixture was extracted with ether (2×50 mL)
  2. dry with materialdried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was then purified by Biotage (0-20% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-8e105f46896141aeb7dfda9e017486b6
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08906929B2

반응 노트

불러오는 중…