Benzyl Bromide → ((Pent-4-yn-1-yloxy)methyl)benzene

HRID 1522999ノート

反応式

HRID 1522999 の反応式
[H-].[Na+].[C:3]([OH:8])#[C:4][CH2:5][CH2:6][CH3:7].[CH:9]1[CH:14]=[CH:13][C:12]([CH2:15]Br)=[CH:11][CH:10]=1>C1COCC1>[CH2:3]([O:8][CH2:15][C:12]1[CH:13]=[CH:14][CH:9]=[CH:10][CH:11]=1)[CH2:4][CH2:5][C:6]#[CH:7]

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 10866258Pentynol

生成物 1

HCID 563055((Pent-4-yn-1-yloxy)methyl)benzene収率 94.5%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a flame-dried round-bottomed flask was added NaH (2 equiv., 47.6 mmol, 1.9 g of a 60% dispersion in mineral oil). The solid was washed with hexanes (15 mL), THF (95 mL) was added and the suspension was cooled to 0° C. Pentynol (1 equiv., 23.8 mmol, 2.0 g) was added drop wise in THF (5 mL), followed by drop wise addition of BnBr (0.92 equiv., 21.9 mmol, 2.60 mL). The reaction was warmed to ambient temperature over 16 h, quenched with saturated aqueous NH4Cl (25 mL), and diluted with water (20 mL). The organic layer was extracted with EtOAc (2×40 mL), washed with brine (40 mL) and dried with Na2SO4. Product isolation was achieved by concentration in vacuo and purification by flash column chromatography to afford ((pent-4-yn-1-yloxy)methyl)benzene (3.60 g, 20.7 mmol, 94%). TLC Rf=0.41 (5% EtOAc/Hex); 1HNMR (300 MHz): δ 7.29-7.44 (5H), 4.55 (s, 2H), 3.61 (t, 2H, J=6.2 Hz), 2.36 (td, 2H, J=7.1, 2.6 Hz), 1.97 (t, 1H, J=2.6 Hz), 1.81-1.93 (m, 2H). 13CNMR (75 MHz): δ 138.5, 128.4, 127.63, 127.58, 84.0, 73.0, 68.7, 68.5, 28.7, 15.3.

後処理

  1. washThe solid was washed with hexanes (15 mL), THF (95 mL)
  2. additionwas added
  3. temperatureThe reaction was warmed to ambient temperature over 16 h
  4. customquenched with saturated aqueous NH4Cl (25 mL)
  5. additiondiluted with water (20 mL)
  6. extractionThe organic layer was extracted with EtOAc (2×40 mL)
  7. washwashed with brine (40 mL)
  8. dry with materialdried with Na2SO4
  9. concentrationProduct isolation was achieved by concentration in vacuo and purification by flash column chromatography

出典と根拠

ORDレコード
ord-1c270ea69f4a471898ae4bfccba67568
出典データセット
uspto-grants-2015_07
特許番号
US09079835B2

反応ノート

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