Hydrochloric Acid → Methyl (3'-benzyloxy-4'-methoxybiphenyl-3-yl)acetate

HRID 2247437ノート

反応式

HRID 2247437 の反応式
[CH2:1]([O:8][CH:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]1([O:18][CH3:19])B(O)O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C(O)C.C(=O)([O-])[O-].[K+].[K+].Br[C:32]1[CH:33]=[C:34]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH:35]=[CH:36][CH:37]=1.Cl>C(OCC)C.COCCOC.[Pd].ClC1[C-](P)C(C2C=CC=CC=2)=C(C2C=CC=CC=2)C=1Cl.[CH-]1C=CC=C1.[Fe+2]>[CH2:1]([O:8][C:9]1[CH:14]=[C:13]([C:36]2[CH:37]=[CH:32][CH:33]=[C:34]([CH2:38][C:39]([O:41][CH3:42])=[O:40])[CH:35]=2)[CH:12]=[CH:11][C:10]=1[O:18][CH3:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 1030Propylene GlycolHCID 11430Potassium CarbonateHCID 11746402Methyl 2-(3-bromophenyl)acetateHCID 686332012-Benzyloxy-1-methoxybenzeneboronic acid

生成物 1

HCID 59219255Methyl (3'-benzyloxy-4'-methoxybiphenyl-3-yl)acetate収率 55.5%

試薬・触媒・溶媒 3

HCID 178527692HCID 178527692、化合物触媒HCID 3283Diethyl Ether溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

1.753 g of 2-Benzyloxy-1-methoxybenzeneboronic acid was suspended in 50 ml of diethyl ether, and 0.49 ml of propylene glycol was added thereto. The mixture was stirred at room temperature for 1 hour, and the solvent was removed to give 2-(3-benzyloxy-4-methoxyphenyl)-[1,3,2]dioxaborynane. This product was dissolved in 30 ml of 1,2-dimethoxyethane, then 1.5 g of potassium carbonate, 1.9 g of methyl 3-bromophenylacetate and 270 mg of dichlorodiphenyl phosphinoferrocene palladium were added thereto, and the mixture was stirred at 80° C. for 3 hours in a nitrogen atmosphere. The reaction mixture was neutralized with 1N hydrochloric acid and extracted with ethyl acetate. The organic layer was washed with water and dried over anhydrous magnesium sulfate and then filtered, and the filtrate was concentrated. The residue was purified by silica gel column chromatography, to give 1.356 g of the title compound in the 6:1→4:1 fraction.

後処理

  1. customthe solvent was removed
  2. customto give 2-(3-benzyloxy-4-methoxyphenyl)-[1,3,2]dioxaborynane
  3. stirringthe mixture was stirred at 80° C. for 3 hours in a nitrogen atmosphere
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated
  9. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-1e524e2bacc5478e973d7ae9fb5b2da0
出典データセット
uspto-grants-2010_03
特許番号
US07687664B2

反応ノート

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