Water → HCID 66990886、化合物

HRID 444627ノート

反応式

HRID 444627 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 66990886HCID 66990886、化合物収率 115.6%

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 57417360Sodium chloride; water溶媒

実験手順

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),

後処理

  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

出典と根拠

ORDレコード
ord-d562becfaf2a4522a0484b22c6bddc18
出典データセット
uspto-grants-2013_07
特許番号
US08475776B2

反応ノート

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