Nitrogen → 1,6-Bis[4-(3-hydroxypropyl)phenoxy]hexane

HRID 32786

反応式

HRID 32786 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][OH:11])=[CH:4][CH:3]=1.I[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18]I.N#N.[C:22](=[O:25])([O-])[O-].[K+].[K+]>CS(C)=O>[OH:11][CH2:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][O:1][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:22][OH:25])=[CH:4][CH:3]=2)=[CH:7][CH:6]=1

参加物

6

反応物 4

HCID 947NitrogenHCID 11430Potassium CarbonateHCID 123731,6-DiiodohexaneHCID 824523-(4-Hydroxyphenyl)propanol

生成物 1

HCID 219598591,6-Bis[4-(3-hydroxypropyl)phenoxy]hexane収率 65%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

A solution of 3-(4-hydroxyphenyl)-1-propanol 35 (3.3 g, 21.7 mmole) and 1,6-di-iodohexane (3.5 g, 8.88 mmole) in dimethylsulfoxide (40 mL) was degassed and saturated with N2 gas and potassium carbonate (4.5 g, 32.56 mmole) was added. The reaction mixture was stirred at 80° C. for 18 h under nitrogen atmosphere and then quenched with brine (150 mL). The product was extracted with EtOAc (200 mL) and the organic extracts were washed with 0.1 M NaOH and brine, and dried with MgSO4. The organics were removed in vacuo to give a pale brown solid. The solid was purified by flash silica column chromatography: 4/1 hexane/EtOAc to 5% MeOH in 1/1 hexane/EtOAc to give 1,6-bis[4-(3-hydroxypropyl)phenoxy]hexane 36 (Rf=0.17 in 1/1 hexane/EtOAc) in 65% yield (2.23 g). 1H-NMR (CD3OD, 299.96 MHz): δ (ppm) 7.08-7.05 (d, 4H), 6.80-6.77 (d, 4H), 3.93-3.89 (t, 4H), 3.56-3.52 (t, 4H), 2.64-2.56 (t, 4H), 1.81-1.69 (m, 8H), 1.44-1.21 (m, 4H).

後処理

  1. additionwas added
  2. customquenched with brine (150 mL)
  3. extractionThe product was extracted with EtOAc (200 mL)
  4. washthe organic extracts were washed with 0.1 M NaOH and brine
  5. dry with materialdried with MgSO4
  6. customThe organics were removed in vacuo
  7. customto give a pale brown solid
  8. customThe solid was purified by flash silica column chromatography

出典と根拠

ORDレコード
ord-b56f08ef211348ddafa822459d992caa
出典データセット
uspto-grants-2008_09
特許番号
US07427639B2

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