Dichloromethane → HCID 67282369, 화합물

HRID 913029노트

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HRID 913029 반응식
[CH2:1]([O:8][C:9]1[C:14](=[O:15])[CH:13]=[CH:12][NH:11][C:10]=1[CH3:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:23]([CH:27](OC)[OH:28])([F:26])([F:25])[F:24].ClCCl>O>[CH2:1]([O:8][C:9]1[C:14](=[O:15])[C:13]([CH:27]([OH:28])[C:23]([F:26])([F:25])[F:24])=[CH:12][NH:11][C:10]=1[CH3:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 98922,2,2-Trifluoro-1-methoxyethanolHCID 11430Potassium CarbonateHCID 27264163-(Benzyloxy)-2-methylpyridin-4(1H)-one

생성물 1

HCID 67282369HCID 67282369, 화합물수율 24%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of 3-benzyloxy-2-methyl-1H-pyridin-4-one (10.0 g, 46.4 mmol), potassium carbonate (19 g, 138 mmol), and CF3CH(OH)OCH3 (35 mL, 0.35 mol) in a 500 mL 3-necked round bottom flask equipped with a mechanical stirrer was heated to reflux for 6 days. The progress of the reaction was monitored by HPLC Method 3 (Example 24). Analysis of the HPLC data indicated that there was about 42% conversion. The reaction was stopped, and dichloromethane and deionized water were added. The organic fraction was collected, washed with brine, dried over Na2SO4, filtered and concentrated to dryness. Purification of the residue by column chromatography on silica (methanol/dichloromethane 2/100 to 5/100 v:v) afforded 3-benzyloxy-2-methyl-5-(2,2,2-trifluoro-1-hydroxy-ethyl)-1H-pyridin-4-one as a solid product (3.5 g, 24% yield, HPLC Method 3 (Example 24), RT=14.3 min). 1H NMR (DMSO-d6) 8 ppm: 11.68 (br s, 1H), 7.58 (s, 1H), 7.35, (m, 5H), 5.34 (q, J=7.3 Hz, 1H), 5.06 (m, 2H), 2.08 (s, 3H); MS-ESI (m/z) 313.7 [M+1]+, 206.1, 91.1 (100%).

후처리

  1. customequipped with a mechanical stirrer
  2. temperaturewas heated
  3. temperatureto reflux for 6 days
  4. additionwere added
  5. customThe organic fraction was collected
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated to dryness
  10. customPurification of the residue by column chromatography on silica (methanol/dichloromethane 2/100 to 5/100 v:v)

출처 및 근거

ORD 기록
ord-205ab1b1ff904283a7960ee3f2f451c1
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026261B2

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