Epichlorohydrin → 2-[[4-(2-Fluoroethoxy)phenoxy]methyl]oxirane

HRID 1774310ノート

反応式

HRID 1774310 の反応式
[OH-].[Na+].[F:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=1.[CH2:14]([CH:16]1[O:18][CH2:17]1)Cl.CCOC(C)=O>O>[F:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH:16]2[CH2:17][O:18]2)=[CH:9][CH:8]=1

参加物

6

反応物 4

HCID 7835EpichlorohydrinHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 150586584-(2-Fluoroethoxy)phenol

生成物 1

HCID 867130932-[[4-(2-Fluoroethoxy)phenoxy]methyl]oxirane収率 48%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
100 °C

実験手順

A solution of NaOH (0.35 g) in 10 mL of water was added to a mixture of 4-(2-f luoroethoxy) phenol (1.10 g, 7.1 mmol) and epichlorohydrin (0.80 mL, 10.2 mmol). The mixture was heated at 100° C. for 3 h. After cooling, the mixture is taken up with AcOEt (50 mL). The organic phase was separated, washed with brine, dried over Na2SO4 and evaporated under reduced pressure. The crude residue was chromatographed (Petroleum ether/AcOEt, 4:1, as eluent) to afford pure compound in 48% yield. 1H NMR (CDCl3): δ 2.60-2.70 (m, 2H), 3.16 (m, 1H), 3.89-4.04 (m, 2H), 4.17-4.28 (m, 1H), 4.50-4.65 (m, 1H), 6.54 -6.60 (m, 2H), 6.84-6.87 (m, 2H).

後処理

  1. temperatureAfter cooling
  2. customThe organic phase was separated
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated under reduced pressure
  6. customThe crude residue was chromatographed (Petroleum ether/AcOEt, 4:1, as eluent)
  7. customto afford pure compound in 48% yield

出典と根拠

ORDレコード
ord-c8ad2e8ee1c1450c8a3355303c420a31
出典データセット
uspto-grants-2016_02
特許番号
US09260400B2

反応ノート

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