Cesium carbonate → tert-butyl 5'-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-2-enoyl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

HRID 1508301노트

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HRID 1508301 반응식
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9]1([CH2:15][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:13]1)[O:8][CH2:7]2)(=[O:3])[CH3:2].[Cl:23][C:24]1[CH:25]=[C:26]([C:31](=O)[C:32]([F:35])([F:34])[F:33])[CH:27]=[C:28]([Cl:30])[CH:29]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.FC(F)(F)C1C=CC=CC=1>[Cl:23][C:24]1[CH:25]=[C:26]([C:31]([C:32]([F:35])([F:33])[F:34])=[CH:2][C:1]([C:4]2[CH:5]=[C:6]3[C:10](=[CH:11][CH:12]=2)[C:9]2([CH2:13][N:14]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:15]2)[O:8][CH2:7]3)=[O:3])[CH:27]=[C:28]([Cl:30])[CH:29]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 27582311-(3,5-Dichlorophenyl)-2,2,2-trifluoroethan-1-oneHCID 70663143tert-butyl 5'-acetyl-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate

생성물 1

HCID 90001161tert-butyl 5'-(3-(3,5-dichlorophenyl)-4,4,4-trifluorobut-2-enoyl)-3'H-spiro[azetidine-3,1'-isobenzofuran]-1-carboxylate수율 44%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 7368(Trifluoromethyl)benzene용매

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온도
110 °C

실험 절차

In 100 mL two neck RBF equipped with dean-stark apparatus, the stirred solution of tert-butyl 5′-acetyl-3′H-spiro[azetidine-3,1′-isobenzofuran]-1-carboxylate (Preparation 1, 6.65 g, 21.95 mmol) in toluene (20 mL) and trifluorotoluene (20 mL) was added 1-(3,5-dichloro-phenyl)-2,2,2-trifluoro-ethanone (6.133 g, 25.24 mmol) and Cs2CO3 (0.71 g, 2.20 mmol) at room temperature. Resulting reaction mixture was stirred at 110° C. for 16 hours. After complete consumption of starting material, the reaction mixture was diluted with tert-butylmethyl ether (60 mL) and filtered through celite bed. Filtrate was concentrated to get as brown sticky oil (7.2 g, crude). Crude compound was purified by column chromatography using silica gel (230-400 mesh). Desired compound was eluted in 20% ethyl acetate in n-hexane to give light yellow solid (5.1 g, 43.97%). LC-MS (m/z): 525.9 (M−H).

후처리

  1. customResulting
  2. customreaction mixture
  3. customAfter complete consumption of starting material
  4. additionthe reaction mixture was diluted with tert-butylmethyl ether (60 mL)
  5. filtrationfiltered through celite bed
  6. concentrationFiltrate was concentrated
  7. customto get as brown sticky oil (7.2 g, crude)
  8. customCrude compound was purified by column chromatography
  9. washDesired compound was eluted in 20% ethyl acetate in n-hexane

출처 및 근거

ORD 기록
ord-9b32e69de5de4989ba94334713c26026
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09221835B2

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