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

HRID 991588노트

반응식

HRID 991588 반응식
[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]

참가 물질

5

반응물 3

HCID 8085DiisobutylamineHCID 24648Sulfuryl chloride2회HCID 227373584-(Oxan-4-yl)phenol

생성물 1

HCID 184146372-Chloro-4-(oxan-4-yl)phenol수율 78.9%

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
70 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-76698d8fdca94847baf91ee1b2cf2f62
출처 데이터셋
uspto-grants-2002_10
특허 번호
US06465497B2

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