Iodine → 2-(2-Cyclobutyl-6-fluoro-4-methoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

HRID 586701

반응식

HRID 586701 반응식
[CH:1]1(Cl)[CH2:4][CH2:3][CH2:2]1.[Mg].II.[F:9][C:10]1[CH:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20](F)[C:11]=1[C:12]([NH:14][C:15]([CH3:19])([CH3:18])[CH2:16][OH:17])=O.[Na+].[Na+].C(N(CC(O)=O)CC(O)=O)CN(CC([O-])=O)CC([O-])=O>O1CCCC1.[OH-].[Na+]>[CH:1]1([C:20]2[CH:21]=[C:22]([O:24][CH3:25])[CH:23]=[C:10]([F:9])[C:11]=2[C:12]2[O:17][CH2:16][C:15]([CH3:19])([CH3:18])[N:14]=2)[CH2:4][CH2:3][CH2:2]1

참가 물질

8

반응물 5

HCID 807IodineHCID 70712ChlorocyclobutaneHCID 5462224MagnesiumHCID 13020083Ethylenediaminetetraacetic acid disodium saltHCID 223353682,6-Difluoro-N-(2-hydroxy-1,1-dimethylethyl)-4-methoxybenzamide

생성물 1

HCID 223351682-(2-Cyclobutyl-6-fluoro-4-methoxyphenyl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 14798Sodium Hydroxide용매

실험 절차

To a solution of cyclobutyl chloride (5.64 g, 62 mmol) in anhydrous tetrahydrofuran (60 mL) was added magnesium turnings (1.56 g, 65 mmol) followed by a crystal of iodine, at room temperature. The mixture was stirred at room temperature for 1 hour, followed by a further hour under reflux. A solution of the fluoro compound from preparation 2 (7.23 g, 30 mmol) in tetrahydrofuran (80 mL) was cooled in an ice-bath to 0° C., and the grignard solution (40 mL) was added dropwise over 15 minutes, the cooling bath was removed and reaction warmed to room temperature and stirred for 2 hours. Further grignard solution (10 mL) was added and the reaction stirred for a further 30 minutes. The reaction was poured into a solution of ethylenediaminetetraacetic acid disodium salt (12 g) in 1N sodium hydroxide (100 mL), and the mixture extracted with ethyl acetate (1×200 mL, 2×100 mL). The combined organic extracts were dried (MgSO4) and evaporated under reduced pressure, to afford the title compound as a pale yellow oil, 8.31 g.

후처리

  1. waitfollowed by a further hour
  2. temperatureunder reflux
  3. temperaturewas cooled in an ice-bath to 0° C.
  4. customthe cooling bath was removed
  5. customreaction
  6. temperaturewarmed to room temperature
  7. stirringstirred for 2 hours
  8. stirringthe reaction stirred for a further 30 minutes
  9. extractionthe mixture extracted with ethyl acetate (1×200 mL, 2×100 mL)
  10. dry with materialThe combined organic extracts were dried (MgSO4)
  11. customevaporated under reduced pressure

출처 및 근거

ORD 기록
ord-f2e47dd7e7a041c39b3b1550c6f256fa
출처 데이터셋
uspto-grants-2005_08
특허 번호
US06936619B2

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