Formic Acid → 5-Hydroxymethyl-6-phenyl-2,2,4-trimethyl-1,2-dihydroquinoline

HRID 1966282노트

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HRID 1966282 반응식
[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2OS(C(F)(F)F)(=O)=O)=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:29])=[CH:6][C:7]([CH3:28])([CH3:27])[NH:8]2.C(N(CC)CC)C.C(O)=O>CN(C)C=O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:1][CH2:2][C:3]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[CH:11][CH:10]=[C:9]2[C:4]=1[C:5]([CH3:29])=[CH:6][C:7]([CH3:28])([CH3:27])[NH:8]2

참가 물질

7

반응물 3

HCID 284Formic AcidHCID 8471TriethylamineHCID 584854825-Hydroxymethyl-6-(2-trifluoromethylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline

생성물 1

HCID 580267805-Hydroxymethyl-6-phenyl-2,2,4-trimethyl-1,2-dihydroquinoline

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

5-Hydroxymethyl-6-(2-trifluoromethylsulfonyloxyphenyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 6-1, 136 mg, 0.318 mmol) was dissolved in anhydrous N,N-dimethylformamide (1.5 mL), then the solvent was bubbled with argon for 2 minutes, and then tetrakis(triphenylphosphine)palladium(0) (35.6 mg, 0.0308 mmol), triethylamine (221 μL, 1.59 mmol) and formic acid (60 μL, 1.6 mmol) were added thereto. After the reaction mixture was stirred at 60° C. for 10 hours, it was diluted with ethyl acetate (50 mL). The whole was washed with saturated NaHCO3 solution (30 mL) and saturated brine (30 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 (93.0 mg) as a yellow oil. (quantative)

후처리

  1. customthe solvent was bubbled with argon for 2 minutes
  2. washThe whole was washed with saturated NaHCO3 solution (30 mL) and saturated brine (30 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)

출처 및 근거

ORD 기록
ord-08a6d1858ac5446bad50ae03fbcac866
출처 데이터셋
uspto-grants-2013_04
특허 번호
US08420635B2

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