Sodium Iodide → Benzyl 3-chloro-5-(3-hydroxypropoxy)benzoate

HRID 1698859ノート

反応式

HRID 1698859 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([OH:18])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:26][CH2:27][CH2:28][OH:29].[I-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:15]=[C:16]([O:18][CH2:26][CH2:27][CH2:28][OH:29])[CH:17]=1)[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6]

参加物

6

反応物 4

HCID 5238Sodium IodideHCID 10796Cesium carbonate3 回HCID 123083-Bromo-1-propanol2 回HCID 18322181Benzyl 3-chloro-5-hydroxybenzoate

生成物 1

HCID 18322176Benzyl 3-chloro-5-(3-hydroxypropoxy)benzoate

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
50 °C

実験手順

To a solution of phenol 25 (8.80 g, 33.0 mmol) and 3-bromno-1-propanol (2.9 mL, 33 mmol) in acetonitrile (300 nL) was added solid cesium carbonate (12 g, 37 mmol). After stirring 16hrs at 50° C., more 3-bromo-1-propanol (3.3 mmol) and cesium carbonate (3.3 mmol) were added and the reaction stirred another 2 hrs. After adding more 3-bromo-1-propanol and cesium carbonate (3.3 mmol each) and sodium iodide (3.3 mmol), the reaction was stirred 30 minutes at 65° C., then cooled and filtered. The filtrate was evaporated in vacuo, the residue dissolved in ethyl acetate, washed with water, and the organic layer dried over Na2SO4 and filtered. The evaporated filtrate then gave product 26 (5.96 g 56%). 1H NMR (300 MHz, CDCl3) δ 7.63 (t, 1H, J=1.5 Hz), 7.48 (dd, 1H, J=2.4 Hz, 1.4 Hz), 7.46-7.31 (m, 5H), 7.09 (t, 1H, J=2.4 Hz), 5.35 (s, 2H), 4.14 (t, 2H, J =6.0 Hz), 3.85 (t, 2H, J=6.0 Hz), 2.05 (pentet, 2H, J=6.0 Hz).

後処理

  1. stirringthe reaction stirred another 2 hrs
  2. stirringthe reaction was stirred 30 minutes at 65° C.
  3. temperaturecooled
  4. filtrationfiltered
  5. customThe filtrate was evaporated in vacuo
  6. dissolutionthe residue dissolved in ethyl acetate
  7. washwashed with water
  8. dry with materialthe organic layer dried over Na2SO4
  9. filtrationfiltered

出典と根拠

ORDレコード
ord-1296ac4b59674eb2b02118fe501f2986
出典データセット
uspto-grants-2002_02
特許番号
US06344466B2

反応ノート

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