Water → 4-Tert-butyl-2-chloromethyl-5-hydroxy-2,3-dihydrobenzofuran

HRID 1376966노트

반응식

HRID 1376966 반응식
N1C=CC=CC=1.[C:7]([C:11]1[C:16]2[CH2:17][CH:18]([CH2:20]O)[O:19][C:15]=2[CH:14]=[CH:13][C:12]=1[OH:22])([CH3:10])([CH3:9])[CH3:8].S(Cl)([Cl:25])=O.O>C1C=CC=CC=1>[C:7]([C:11]1[C:16]2[CH2:17][CH:18]([CH2:20][Cl:25])[O:19][C:15]=2[CH:14]=[CH:13][C:12]=1[OH:22])([CH3:10])([CH3:9])[CH3:8]

참가 물질

6

반응물 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 229186574-Tert-butyl-5-hydroxy-2-hydroxymethyl-2,3-dihydrobenzofuran

생성물 1

HCID 229186814-Tert-butyl-2-chloromethyl-5-hydroxy-2,3-dihydrobenzofuran수율 61.2%

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

Pyridine (180 mg, 2.2 mmol) was added to a solution of 4-tert-butyl-5-hydroxy-2-hydroxymethyl-2,3-dihydrobenzofuran (430 mg, 1.9 mmol) in benzene (15 ml) and, subsequently, thionyl chloride (310 mg, 2.6 mmol) was added dropwise under ice cooling. After being allowed to warm to room temperature, the mixture was heated under reflux for 24 h. After cooling, water was added and the solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and water, then dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (chloroform) to afford 4-tert-butyl-2-chloromethyl-5-hydroxy-2,3-dihydrobenzofuran [280 mg (yield, 61%)] as a colorless oil.

후처리

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 h
  3. temperatureAfter cooling
  4. extractionthe solution was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel chromatography (chloroform)

출처 및 근거

ORD 기록
ord-226c5ba4f2ca4f6d9677474129b07d54
출처 데이터셋
uspto-grants-1997_09
특허 번호
US05663373

반응 노트

불러오는 중…