Triphenylphosphine → ethyl 3-(4-{[2',6'-dimethyl-4'-(tetrahydro-2H-thiopyran-4-yloxy)biphenyl-3-yl]methoxy}-2-fluorophenyl)propanoate

HRID 273422

반응식

HRID 273422 반응식
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH2:9][C:10]2[CH:11]=[C:12]([C:16]3[C:21]([CH3:22])=[CH:20][C:19]([OH:23])=[CH:18][C:17]=3[CH3:24])[CH:13]=[CH:14][CH:15]=2)[CH:5]=[CH:4][C:3]=1[CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].[S:32]1[CH2:37][CH2:36][CH:35](O)[CH2:34][CH2:33]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:22][C:21]1[CH:20]=[C:19]([O:23][CH:35]2[CH2:36][CH2:37][S:32][CH2:33][CH2:34]2)[CH:18]=[C:17]([CH3:24])[C:16]=1[C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH2:9][O:8][C:6]2[CH:5]=[CH:4][C:3]([CH2:25][CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[C:2]([F:1])[CH:7]=2)[CH:11]=1

참가 물질

6

반응물 4

HCID 11776Triphenylphosphine2회HCID 220568ethyl N-ethoxycarbonyliminocarbamate2회HCID 576296Tetrahydro-2H-thiopyran-4-ol2회HCID 58903128Ethyl 3-{2-fluoro-4-[(4'-hydroxy-2',6'-dimethylbiphenyl-3-yl)methoxy]phenyl}propanoate

생성물 1

HCID 58903212ethyl 3-(4-{[2',6'-dimethyl-4'-(tetrahydro-2H-thiopyran-4-yloxy)biphenyl-3-yl]methoxy}-2-fluorophenyl)propanoate수율 91%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of ethyl 3-{2-fluoro-4-[(4′-hydroxy-2′,6′-dimethylbiphenyl-3-yl)methoxy]phenyl}propanoate (0.50 g, 1.18 mmol), tetrahydro-2H-thiopyran-4-ol (0.15 g, 1.30 mmol) and triphenylphosphine (0.31 g, 1.30 mmol) in tetrahydrofuran (10 mL) was added diethyl azodicarboxylate (40% toluene solution, 0.70 mL, 1.53 mmol) at room temperature with stirring. The reaction mixture was stirred at room temperature for 19 hrs., and an equivalent amount of the aforementioned reagents (tetrahydro-2H-thiopyran-4-ol, triphenylphosphine and diethyl azodicarboxylate) were added. The mixture was further stirred at the same temperature for 6 hrs. The reaction mixture was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=3/1) to give the title compound (0.53 g, yield 91%) as a yellow oil.

후처리

  1. stirringThe reaction mixture was stirred at room temperature for 19 hrs
  2. stirringThe mixture was further stirred at the same temperature for 6 hrs
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=10/1-hexane/ethyl acetate=3/1)

출처 및 근거

ORD 기록
ord-ad2800bd3659447dbd57b476f3d4122d
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07456218B2

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