Ethanol → 4-(3-Benzyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol

HRID 383228노트

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HRID 383228 반응식
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([C:6]2[CH2:7][O:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[C:11](O)[CH:10]=3)=[CH:4][CH:3]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[CH2:27]=[O:28].[CH2:29](O)C>>[CH2:19]([N:26]1[CH2:29][C:12]2[CH:13]=[C:14]3[C:9](=[CH:10][C:11]=2[O:28][CH2:27]1)[O:8][CH2:7][C:6]([C:5]1[CH:17]=[CH:18][C:2]([OH:1])=[CH:3][CH:4]=1)=[CH:15]3)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

5

반응물 4

HCID 702Ethanol2회HCID 712FormaldehydeHCID 7504BenzylamineHCID 219100Phenoxodiol2회

생성물 1

HCID 250064744-(3-Benzyl-2,3,4,8-tetrahydrochromeno[6,7-e][1,3]oxazin-7-yl)phenol

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온도
85 °C

실험 절차

4′,7-Dihydroxyisoflav-3-ene (0.47 g, 1.97 mmol) was dissolved in ethanol (ca. 40 mL) and heated to 80-90° C. A solution of benzylamine (0.44 mL, 3.5 mmol) and 37% formaldehyde (0.35 mL, 12.7 mmol) in ethanol (ca. 20 mL) was added to the dehydroequol solution. The reaction mixture was refluxed for approximately 7 hours and after cooling to room temperature the volume was concentrated in vacuo. The mixture was left in the fridge to crystallise. The yellow solid was collected under suction and the filtrate evaporated to dryness to obtain a second crop of the title compound, (combined yield 0.17 g, 23%).

후처리

  1. temperatureThe reaction mixture was refluxed for approximately 7 hours
  2. temperatureafter cooling to room temperature the volume
  3. concentrationwas concentrated in vacuo
  4. waitThe mixture was left in the fridge
  5. customto crystallise
  6. customThe yellow solid was collected under suction
  7. customthe filtrate evaporated to dryness

출처 및 근거

ORD 기록
ord-c6eb609a9c764f31bf1e3a52ab7d10d8
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367659B2

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