Sodium Carbonate → (4'-(Benzyloxy)-2,2',6'-trimethylbiphenyl-3-yl)methanol

HRID 2280655ノート

反応式

HRID 2280655 の反応式
[CH3:1][C:2]1[C:7](Br)=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][OH:10].[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([CH3:25])[C:22](B(O)O)=[C:21]([CH3:29])[CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>CN(C)C=O.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].O>[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([C:7]2[CH:6]=[CH:5][CH:4]=[C:3]([CH2:9][OH:10])[C:2]=2[CH3:1])=[C:21]([CH3:29])[CH:20]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

8

反応物 4

HCID 10340Sodium CarbonateHCID 10035697(3-Bromo-2-methylphenyl)methanolHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 23157199(4-(Benzyloxy)-2,6-dimethylphenyl)boronic acid

生成物 1

HCID 89701782(4'-(Benzyloxy)-2,2',6'-trimethylbiphenyl-3-yl)methanol収率 57.2%

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

2-Methyl-3-bromo-phenylmethanol (201 mg, 1 mmol, prepared by a method disclosed in PCT patent application WO2010143733), (4-(benzyloxy)-2,6-dimethylphenyl) boronic acid 12b (300 mg, 1.20 mmol), 1 mL of 2M aqueous sodium carbonate solution, 2-dicyclohexylphosphino-2′,6′-dimethoxy-1,1′-biphenyl (33 mg, 0.08 mmol) and tris(dibenzylideneacetone)dipalladium (18 mg, 0.02 mmol) were dissolved in 1 mL of N,N-dimethylformamide. The reaction mixture was reacted at 120° C. under microwave conditions for 1 hour. The resulting mixture was mixed with 10 mL of water and extracted with ethyl acetate (20 mL×2). The combined organic extracts were washed with saturated sodium chloride solution (30 mL), dried with anhydrous magnesium sulphate, and filtered. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography with elution system B to obtain the title compound (4′-(benzyloxy)-2,2′,6′-trimethylbiphenyl-3-yl)methanol 12c (190 mg, yield 57.2%) as a red slime.

後処理

  1. customThe reaction mixture was reacted at 120° C. under microwave conditions for 1 hour
  2. extractionextracted with ethyl acetate (20 mL×2)
  3. washThe combined organic extracts were washed with saturated sodium chloride solution (30 mL)
  4. dry with materialdried with anhydrous magnesium sulphate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography with elution system B

出典と根拠

ORDレコード
ord-6e7a7ffad3c14926aa54fe3ba7a43d0f
出典データセット
uspto-grants-2015_09
特許番号
US09139548B2

反応ノート

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