Water → HCID 66990886, 화합물

HRID 444627노트

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HRID 444627 반응식
[CH2:1]([O:8][C:9]1[C:14](OC)=[CH:13][C:12](B(O)O)=[C:11]([O:20][CH3:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:22][O:23][C:24](=[O:42])[C:25]1[CH:30]=[C:29]([C:31](=[O:33])[CH3:32])[CH:28]=[CH:27][C:26]=1OS(C(F)(F)F)(=O)=O.C([O-])([O-])=O.[K+].[K+].O>[Cl-].[Na+].O.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.C(OCC)(=O)C>[CH3:22][O:23][C:24]([C:25]1[C:26]([C:12]2[CH:13]=[CH:14][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[CH:10][C:11]=2[O:20][CH3:21])=[CH:27][CH:28]=[C:29]([C:31](=[O:33])[CH3:32])[CH:30]=1)=[O:42]

참가 물질

8

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 10935085B-[2,5-Dimethoxy-4-(phenylmethoxy)phenyl]boronic acidHCID 11438780methyl 5-acetyl-2-{[(trifluoromethyl)-sulfonyl]oxy}benzoate

생성물 1

HCID 66990886HCID 66990886, 화합물수율 115.6%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 8857Ethyl Acetate용매HCID 57417360Sodium chloride; water용매

실험 절차

4-Benzyloxy-2,5-dimethoxyphenylboronic acid 5b (4.15 g, 14.4 mmol), 5-Acetyl-2-trifluoromethanesulfonyloxy-benzoic acid methyl ester 6 (4.69 g, 14.4 mmol) and K2CO3 (3.98 g, 28.8 mmol) were added and the flask was flushed with Ar. Absolute ethanol (83 mL) and DME (94 mL) were added followed by Pd (PPh3)4 (0.87 g, 0.785 mmol) and the reaction mixture refluxed for 4 h. After cooling, water (100 ml), ethyl acetate (100 mL) and brine (50 mL) were added. The organic layer was washed with brine (2×50 mL) and the combined aqueous fraction was back extracted with ethyl acetate. The combined organic fraction was dried, concentrated and recrystallized from ethyl acetate/hexanes to give 6.5 g (99%) of 7b as a yellow solid. 1H-NMR (400 MHz, CDCl3) dH 2.65 (3H, s, COCH3), 3.58 (3H, s, OCH3), 3.68 (3H, s, OCH3), 3.88 (3H, s, OCH3), 5.21 (21H, s, CH2Ph), 6.55 (1H, s, ArH), 6.86 (1H, s, ArH), 7.30-7.48 (6H, m, ArH+CH2Ph), 8.10 (1H, d, ArH),8.37(1H,s,ArH),

후처리

  1. customthe flask was flushed with Ar
  2. additionAbsolute ethanol (83 mL) and DME (94 mL) were added
  3. temperaturethe reaction mixture refluxed for 4 h
  4. temperatureAfter cooling
  5. washThe organic layer was washed with brine (2×50 mL)
  6. extractionthe combined aqueous fraction was back extracted with ethyl acetate
  7. customThe combined organic fraction was dried
  8. concentrationconcentrated
  9. customrecrystallized from ethyl acetate/hexanes

출처 및 근거

ORD 기록
ord-d562becfaf2a4522a0484b22c6bddc18
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08475776B2

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