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

HRID 383229노트

반응식

HRID 383229 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.[CH3:19][NH:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[CH2:28]=[O:29].[CH2:30](O)C>>[C:22]1([CH:21]([N:20]2[CH2:19][C:12]3[CH:13]=[C:14]4[C:9](=[CH:10][C:11]=3[O:29][CH2:28]2)[O:8][CH2:7][C:6]([C:5]2[CH:17]=[CH:18][C:2]([OH:1])=[CH:3][CH:4]=2)=[CH:15]4)[CH3:30])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

5

반응물 4

HCID 702Ethanol2회HCID 712FormaldehydeHCID 7669N-MethylbenzylamineHCID 219100Phenoxodiol2회

생성물 1

HCID 248965814-(3-(1-Phenylethyl)-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 (0.45 g, 1.87 mmol) was dissolved in ethanol (ca 40 mL) and heated to 80-90° C. A solution of methylbenzylamine (0.44 mL, 4.03 mmol) and 37% formaldehyde (0.35 mL, 123 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-b6c6448adf474d74b28f8268ff7e64f2
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367659B2

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