Diethyl Ether → 8-Methoxymethoxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one

HRID 1043673ノート

反応式

HRID 1043673 の反応式
[OH:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[C:16]1[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH3:21])([CH3:20])[CH:10]=[C:9]3[CH3:22])[C:6](=[O:23])[O:5]2.C(=O)([O-])[O-].[K+].[K+].[C:30]([O:33][CH2:34]C)(=O)C.C(OCC)C>CN(C)C=O>[CH3:30][O:33][CH2:34][O:1][C:2]1[CH:3]=[C:4]2[C:17](=[CH:18][CH:19]=1)[C:16]1[C:7](=[C:8]3[C:13](=[CH:14][CH:15]=1)[NH:12][C:11]([CH3:20])([CH3:21])[CH:10]=[C:9]3[CH3:22])[C:6](=[O:23])[O:5]2

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 579906118-Hydroxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one

生成物 1

HCID 579906038-Methoxymethoxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one収率 66%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

A mixture of 8-hydroxy-2,2,4-trimethyl-1,2-dihydro-6-oxa-1-azachrysen-5-one (Reference Compound No. 1-(4), 1.00 g, 3.25 mmol), chlorodimethylether (420 μL, 5.53 mmol) and potassium carbonate (1.35 g, 9.77 mmol) was suspended in anhydrous N,N-dimethylformamide (15 mL) and the suspension was stirred at 50° C. overnight. After cooling down, ethyl acetate (100 mL) and diethylether (100 mL) were added thereto. The whole was washed with water (150 mL, 100 mL) and saturated brine (100 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (747 mg) as a yellow solid. (Yield 66%)

後処理

  1. temperatureAfter cooling down
  2. washThe whole was washed with water (150 mL, 100 mL) and saturated brine (100 mL) successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

出典と根拠

ORDレコード
ord-f4c9a8ecc7c944298409d2cfe1f2abf0
出典データセット
uspto-grants-2013_10
特許番号
US08563551B2

反応ノート

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