Methanol → HCID 25128918、化合物

HRID 587944ノート

反応式

HRID 587944 の反応式
[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]

参加物

6

反応物 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 25128917HCID 25128917、化合物

生成物 1

HCID 25128918HCID 25128918、化合物

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
22 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6635e1b95ff04b5496d9222a5ebb4e2b
出典データセット
uspto-grants-2016_01
特許番号
US09227918B2

反応ノート

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