Methanol → HCID 25128918, 화합물

HRID 587944노트

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HRID 587944 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[CH2:6][CH2:7][N:8]([CH3:31])[CH2:9][CH2:10][CH2:11][C:12]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)(C(OC)=O)[C:13]([O:15][CH3:16])=[O:14].CO.[H-].[Na+]>C1COCC1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:32]=[CH:33][C:34]=1[O:35][CH3:36])[CH2:6][CH2:7][N:8]([CH3:31])[CH2:9][CH2:10][CH2:11][CH:12]([C:21]1[CH:26]=[CH:25][C:24]([O:27][CH3:28])=[C:23]([O:29][CH3:30])[CH:22]=1)[C:13]([O:15][CH3:16])=[O:14]

참가 물질

6

반응물 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 25128917HCID 25128917, 화합물

생성물 1

HCID 25128918HCID 25128918, 화합물

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

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온도
22 °C

실험 절차

To a solution of 0.349 g (0.694 mmol) of 3a in 20 mL of THF at 22° C. was added 0.281 mL (6.94 mmol) of methanol followed by 56 mg (1.39 mmol) of NaH (60% dispersion in mineral oil). The reaction was refluxed for 1 h, cooled to 22° C. and diluted with 100 mL of DCM. The mixture was washed with 50 mL of saturated NaHCO3, 50 mL of water, dried, and evaporated to give an oil. The oil was purified by flash chromatography on silica gel, eluting first with 2% methanol/DCM and then gradually increasing to 4% methanol/DCM to give 3b as a colorless oil; MS found M+H=446. The oxalate salt of 3r was recrystallized from ethyl acetate; mp 112-113.5° C.

후처리

  1. temperatureThe reaction was refluxed for 1 h
  2. washThe mixture was washed with 50 mL of saturated NaHCO3, 50 mL of water
  3. customdried
  4. customevaporated
  5. customto give an oil
  6. customThe oil was purified by flash chromatography on silica gel
  7. washeluting first with 2% methanol/DCM
  8. temperaturegradually increasing to 4% methanol/DCM

출처 및 근거

ORD 기록
ord-6635e1b95ff04b5496d9222a5ebb4e2b
출처 데이터셋
uspto-grants-2016_01
특허 번호
US09227918B2

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