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Methanol → HCID 67281011, 화합물

HRID 515489
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HRID 515489 반응식
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([CH2:7][N:8]2[CH2:14][CH2:13][CH2:12][O:11][CH:10]([CH3:15])[C:9]2=O)=[CH:5][CH:4]=1.CO.[OH-].[Na+]>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[CH2:14][CH2:13][CH2:12][O:11][CH:10]([CH3:15])[CH2:9]2)=[CH:17][CH:18]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 66718654HCID 66718654, 화합물

생성물 1

HCID 67281011HCID 67281011, 화합물수율 88%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a solution of 4-(4-methoxy-benzyl)-2-methyl-[1,4]oxazepan-3-one (2.00 g, 8.02 mmol) in tetrahydrofuran (24 ml) was added 1M borane-tetrahydrofuran complex in tetrahydrofuran (27.3 ml, 27.3 mmol) at 0° C. The mixture was stirred at room temperature for 3 hours. After cooling to 0° C., methanol (20 ml) and 6N sodium hydroxide (20 ml) was added carefully. The resulting mixture was refluxed for 2 hours and cooled to room temperature. The solvent was removed under reduced pressure. The residue was partitioned between saturated ammonium chloride solution and ethyl acetate. The organic layer was washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=1/1) to afford 4-(4-methoxybenzyl)-2-methyl-[1,4]oxazepane as colorless oil (1.66 g, 88%).

후처리

  1. temperatureAfter cooling to 0° C.
  2. temperatureThe resulting mixture was refluxed for 2 hours
  3. temperaturecooled to room temperature
  4. customThe solvent was removed under reduced pressure
  5. customThe residue was partitioned between saturated ammonium chloride solution and ethyl acetate
  6. washThe organic layer was washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by silica gel column chromatography (eluant: hexane/ethyl acetate=1/1)

출처 및 근거

ORD 기록
ord-6b08a3eb1700444b906d31a286ca3d4a
출처 데이터셋
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09108957B2

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