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

HRID 1400757ノート

反応式

HRID 1400757 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-8e105f46896141aeb7dfda9e017486b6
出典データセット
uspto-grants-2014_12
特許番号
US08906929B2

反応ノート

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