Potassium Phosphate, Tribasic → Tert-butyl 2-hydroxy-6-[({4'-[(methoxycarbonyl)methyl]-3'-methoxy-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate

HRID 2076626ノート

反応式

HRID 2076626 の反応式
P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2[C:22]2[C:27]([O:28][CH3:29])=[CH:26][CH:25]=[CH:24][C:23]=2OC)CCCCC1.Cl[C:39]1[CH:44]=[CH:43][C:42]([CH2:45][C:46]([O:48][CH3:49])=[O:47])=[C:41]([O:50][CH3:51])[CH:40]=1.[OH:52][C:53]1[C:65]([C:66]([F:69])([F:68])[F:67])=[C:64](COC2C=CC(B3OC(C)(C)C(C)(C)O3)=CC=2)[CH:63]=[CH:62][C:54]=1[C:55]([O:57][C:58]([CH3:61])([CH3:60])[CH3:59])=[O:56]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[OH:52][C:53]1[C:65]([C:66]([F:69])([F:67])[F:68])=[CH:64][CH:63]=[C:62]([CH2:29][O:28][C:27]2[CH:22]=[CH:23][C:24]([C:39]3[CH:44]=[CH:43][C:42]([CH2:45][C:46]([O:48][CH3:49])=[O:47])=[C:41]([O:50][CH3:51])[CH:40]=3)=[CH:25][CH:26]=2)[C:54]=1[C:55]([O:57][C:58]([CH3:59])([CH3:60])[CH3:61])=[O:56]

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 67119177Tert-butyl 2-hydroxy-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-3-(trifluoromethyl)benzoateHCID 85739232Methyl 2-(4-chloro-2-methoxyphenyl)acetate

生成物 1

HCID 67119238Tert-butyl 2-hydroxy-6-[({4'-[(methoxycarbonyl)methyl]-3'-methoxy-1,1'-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate収率 457.4%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒HCID 1140Toluene溶媒

反応条件

温度
70 °C

実験手順

After tripotassium phosphate (127 mg, 0.60 mmol), palladium acetate (8 mg, 0.04 mmol) and 2-(dicyclohexylphosphino)-2′,6′-dimethoxy-1,1′-biphenyl (S-PHOS) (16 mg, 0.04 mmol) were added to a solution of methyl (4-chloro-2-methoxyphenyl)acetate (43 mg, 0.2 mmol) obtained in Example (24-1) and tert-butyl 2-hydroxy-{[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]methyl}-3-(trifluoromethyl)benzoate (100 mg, 0.2 mmol) obtained in Example (22-4) in toluene (2.0 ml), the mixture was stirred at 70° C. for 4 hours. After the temperature of the reaction mixture was returned to room temperature, the mixture was poured into water and extracted with ethyl acetate (three times). The organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution and dried with anhydrous sodium sulfate. The residue obtained by removing the solvent under reduced pressure was purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1) to give tert-butyl 2-hydroxy-6-[({4′-[(methoxycarbonyl)methyl]-3′-methoxy-1,1′-biphenyl-4-yl}oxy)methyl]-3-(trifluoromethyl)benzoate (100 mg, yield: 60%).

後処理

  1. customwas returned to room temperature
  2. extractionextracted with ethyl acetate (three times)
  3. washThe organic layer was successively washed with water (twice) and a saturated aqueous NaCl solution
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe residue obtained
  6. customby removing the solvent under reduced pressure
  7. customwas purified by silica gel column chromatography (eluting solvent: n-hexane/ethyl acetate=2/1)

出典と根拠

ORDレコード
ord-6fc1fda48e5f41e6b4bd20a732a9b081
出典データセット
uspto-grants-2011_04
特許番号
US07923573B2

反応ノート

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