Water → (3RS,4RS)-4-[3-(4-iodobutyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran

HRID 1859321노트

반응식

HRID 1859321 반응식
Cl[CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]2[C:18]3[CH:19]=[CH:20][C:21]([O:23][CH2:24][O:25][CH3:26])=[CH:22][C:17]=3[O:16][CH2:15][C:14]2([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:30][CH:29]=2)[CH3:27])[CH:10]=[CH:11][CH:12]=1.[I-:38].[Na+].O>C(C(C)=O)C>[I:38][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:13]2[C:18]3[CH:19]=[CH:20][C:21]([O:23][CH2:24][O:25][CH3:26])=[CH:22][C:17]=3[O:16][CH2:15][C:14]2([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][O:36][CH3:37])=[CH:30][CH:29]=2)[CH3:27])[CH:10]=[CH:11][CH:12]=1

참가 물질

5

반응물 3

HCID 962WaterHCID 5238Sodium IodideHCID 22123573(3RS,4RS)-4-[3-(4-chlorobutyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran

생성물 1

HCID 22123635(3RS,4RS)-4-[3-(4-iodobutyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran수율 97%

시약·촉매·용매 1

HCID 6569Methyl Ethyl Ketone용매

실험 절차

(3RS,4RS)-4-[3-(4-Chlorobutyloxy)phenyl]-7-methoxymethyloxy-3-[4-(methoxymethyloxy)phenyl]-3-methyl-2,3-dihydro-4H-benzopyran (300 mg, 0.57 mmol) and sodium iodide (260 mg, 1.73 mmol) were dissolved in methyl ethyl ketone (30 ml) and then refluxed for 12 hours. The reaction mixture was cooled to room temperature and then water was added thereto. The reaction solution was extracted with ethyl acetate and the organic layer was dried over anhydrous magnesium sulfate, filtered and then concentrated under reduced pressure to remove the organic solvent. The concentrate was separated by column chromatography (n-hexane:ethyl acetate=4:1) to obtain 340 mg (yield: 97%) of the title compound as a colorless oil.

후처리

  1. temperaturerefluxed for 12 hours
  2. extractionThe reaction solution was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customto remove the organic solvent
  7. customThe concentrate was separated by column chromatography (n-hexane:ethyl acetate=4:1)

출처 및 근거

ORD 기록
ord-cab0e74e91794a688628aed68bc60ff9
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06153768

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