Chlorodifluoromethane → Methyl 9-difluoromethylxanthene-9-carboxylate

HRID 750551

반응식

HRID 750551 반응식
[CH:1]1[C:14]2[CH:13]([C:15]([O:17][CH3:18])=[O:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.CC(C)([O-])C.[K+].[F:25][CH:26]([F:28])Cl>O1CCCC1.O>[F:25][CH:26]([F:28])[C:13]1([C:15]([O:17][CH3:18])=[O:16])[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[O:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

참가 물질

6

반응물 3

HCID 6372ChlorodifluoromethaneHCID 699662methyl 9H-xanthene-9-carboxylateHCID 23665647Potassium tert-butoxide

생성물 1

HCID 68963094Methyl 9-difluoromethylxanthene-9-carboxylate

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

16.8 g (0.07 mol) of methyl 9-xanthenecarboxylate (obtainable according to step 1.1.a) are dissolved in 300 mL of tetrahydrofuran and 9.1 g (0.077 mol) of potassium tert-butoxide are added batchwise while cooling. Then difluorochloromethane is piped in at 0° C. over a period of 1.5 hours. After all the gas has been piped in, the reaction mixture is left to stand for 72 hours at ambient temperature. The reaction mixture is then diluted with water to a total volume of about 2000 mL, extracted with ethyl acetate, the organic phase is separated off and washed with 5% aqueous sodium carbonate solution. After being extracted again with water, the organic phase is dried over magnesium sulfate and the solvent is removed by distillation. The crude product is purified by chromatography on silica gel (eluent: cyclohexane-ethyl acetate (98:2)) or by recrystallization from cyclohexane. Yield: 5.35 g of white crystals (26% of theoretical yield); melting point: 101° C.

후처리

  1. temperaturewhile cooling
  2. waitis left
  3. extractionextracted with ethyl acetate
  4. customthe organic phase is separated off
  5. washwashed with 5% aqueous sodium carbonate solution
  6. extractionAfter being extracted again with water
  7. dry with materialthe organic phase is dried over magnesium sulfate
  8. customthe solvent is removed by distillation
  9. customThe crude product is purified by chromatography on silica gel (eluent: cyclohexane-ethyl acetate (98:2)) or by recrystallization from cyclohexane

출처 및 근거

ORD 기록
ord-7d4ce18d309743089513cffe55a4e21e
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07405224B2

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