Dimethylamine → 9,10-Dihydroanthracene

HRID 10076

反応式

HRID 10076 の反応式
CO[C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([CH2:10]N(C2C=CC(CO)=CC=2)C)=[CH:6][CH:5]=1.CNC.B(Cl)(Cl)Cl.[Na+].[Cl-].O.S(=O)(=O)(O)O>C(Cl)Cl>[CH:3]1[C:4]2[CH2:5][C:6]3[C:7](=[CH:10][CH:6]=[CH:7][CH:8]=3)[CH2:8][C:9]=2[CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 674DimethylamineHCID 1118Sulfuric AcidHCID 25135Boron TrichlorideHCID 57417360Sodium chloride; waterHCID 695206284-{[(4-Hydroxymethyl-phenyl)-methyl-amino]-methyl}-benzoic acid methyl ester

生成物 1

HCID 119409,10-Dihydroanthracene

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To an ice cold solution of 4-{[(4-hydroxymethyl-phenyl)-methyl-amino]-methyl}-benzoic acid methyl ester (0.5 g, 1.8 mmol) and 3-isopropenyl-phenyl)-dimethyl-amine (0.31 g, 1.9 mmol) in methylene chloride (CH2Cl2, 25 mL)) is added dropwise a solution of boron trichloride (1 M BCl3 in CH2Cl2, 2 mL). The reaction mixture is allowed to stir overnight at room temperature cooled to −15° C. (NaCl/water) followed by dropwise addition of concentrated sulfuric acid (12 mL). Methylene chloride is removed and the mixture is allowed to stand at 40° C. over a period of 16 h. The resulting solution is poured into crushed ice and neutralized with 2 N sodium hydroxide. The aqueous solution is extracted with methylene chloride (2×75 ml), dried (Na2SO4) and concentrated giving the 9,10-dihydro-anthracene as a residue.

後処理

  1. customMethylene chloride is removed
  2. waitto stand at 40° C. over a period of 16 h
  3. additionThe resulting solution is poured
  4. custominto crushed ice
  5. extractionThe aqueous solution is extracted with methylene chloride (2×75 ml)
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-ca7acc999d4a4b90bdd5cd77f7621709
出典データセット
uspto-grants-2006_08
特許番号
US07091348B2

関連ノート

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