[1,1'-Biphenyl]-4,4'-dicarboxaldehyde → 4'-Pyrrolidin-1-ylmethyl-biphenyl-4-carbaldehyde

HRID 989269

反応式

HRID 989269 の反応式
[C:1]1([C:9]2[CH:14]=[CH:13][C:12]([CH:15]=O)=[CH:11][CH:10]=2)[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=1.[NH:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1.[B-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].[OH-].[Na+]>C(Cl)Cl.C(O)(=O)C>[N:17]1([CH2:15][C:12]2[CH:13]=[CH:14][C:9]([C:1]3[CH:6]=[CH:5][C:4]([CH:7]=[O:8])=[CH:3][CH:2]=3)=[CH:10][CH:11]=2)[CH2:21][CH2:20][CH2:19][CH2:18]1

参加物

7

反応物 4

HCID 6200[1,1'-Biphenyl]-4,4'-dicarboxaldehydeHCID 14798Sodium HydroxideHCID 31268PyrrolidineHCID 23676153Sodium bis(acetyloxy)boranuidyl acetate

生成物 1

HCID 98139384'-Pyrrolidin-1-ylmethyl-biphenyl-4-carbaldehyde

試薬・触媒・溶媒 2

HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

A solution of biphenyl-4,4′-dicarbaldehyde (0.21 g), pyrrolidine (83 μL), and acetic acid (57 μL) in DCM (5 mL) was treated with sodium triacetoxyborohyride (0.34 g). After 16 hours, the resulting mixture was treated with 3M NaOH (1.5 mL) and extracted with DCM (3×10 mL). The combined organic phases were dried over sodium sulfate and evaporated. The residue was purified via preparative thin layer chromatography eluting with 5% MeOH/DCM to give the title compound (42.5 mg). 1H NMR (400 MHz, CDCI3)δ10.05 (s, 1 H), 7.94 (d, J=8.0, 2 H), 7.75 (d, J=8.0, 2 H), 7.60 (d, J=8.0, 2 H), 7.47 (d, J=8.0, 2 H), 3.72 (s, 2 H), 2.61 (br s, 4 H), 1.84 (br s, 4 H).

後処理

  1. extractionextracted with DCM (3×10 mL)
  2. dry with materialThe combined organic phases were dried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified via preparative thin layer chromatography
  5. washeluting with 5% MeOH/DCM

出典と根拠

ORDレコード
ord-8d576f7fb8994452926dd1480695ef3d
出典データセット
uspto-grants-2003_10
特許番号
US06638967B2

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