Diisobutylamine → 2-Chloro-4-(oxan-4-yl)phenol

HRID 991588ノート

反応式

HRID 991588 の反応式
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][CH:8]=2)[CH2:3][CH2:2]1.C(NCC(C)C)C(C)C.S(Cl)([Cl:26])(=O)=O>C1(C)C=CC=CC=1>[Cl:26][C:9]1[CH:8]=[C:7]([CH:4]2[CH2:5][CH2:6][O:1][CH2:2][CH2:3]2)[CH:12]=[CH:11][C:10]=1[OH:13]

参加物

5

反応物 3

HCID 8085DiisobutylamineHCID 24648Sulfuryl chloride2 回HCID 227373584-(Oxan-4-yl)phenol

生成物 1

HCID 184146372-Chloro-4-(oxan-4-yl)phenol収率 78.9%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

To a 30 ml Toluene solution of 4-(4-tetrahydropyranyl)phenol 1 g (5.61 mmol) and diisobutylamine 0.08 ml (0.46 mmol) was added sulfuryl chloride 0.51 ml (6.35 mmol) over 3 hr period upon heating at 70° C. Stirring was continued at that temp. for 2 hr after the addition of sulfuryl chloride was complete. The solvent was removed under reduced pressure, diluted with ethyl acetate and washed with 2N aqueous HCl, saturated aqueous sodium bicarbonate solution, dried over anhydrous sodium sulfate, filtered, concentrated, chromatographed on silica gel (hexanes: ethyl acetate) to give 0.941 g of the title compound as while solid.

後処理

  1. customThe solvent was removed under reduced pressure
  2. additiondiluted with ethyl acetate
  3. washwashed with 2N aqueous HCl, saturated aqueous sodium bicarbonate solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customchromatographed on silica gel (hexanes: ethyl acetate)

出典と根拠

ORDレコード
ord-76698d8fdca94847baf91ee1b2cf2f62
出典データセット
uspto-grants-2002_10
特許番号
US06465497B2

反応ノート

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