Benzyl diethyl phosphate → 4-Benzyl-furan-2-carbaldehyde

HRID 2105557

反応式

HRID 2105557 の反応式
[CH:1]([C:3]1[O:7][CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=1)=[O:2].P(OCC)(OCC)(O[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=O.C(C1OC(C=O)=CC=1)C1C=CC=CC=1>CC#N.C(O)(C)C.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:20]([C:5]1[CH:4]=[C:3]([CH:1]=[O:2])[O:7][CH:6]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

参加物

6

反応物 3

HCID 298808Benzyl diethyl phosphateHCID 35475414-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)furan-2-carbaldehydeHCID 124185375-Benzylfuran-2-carbaldehyde

生成物 1

HCID 596485854-Benzyl-furan-2-carbaldehyde収率 41%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 21921005Acetonitrile 2-propanol溶媒

実験手順

The title compound was synthesized from 5-formylfuran-3-boronic acid pinacol ester (878 mg, 3.95 mmol), and benzyl diethyl phosphate (1.25 g, 5.14 mmol) using the same conditions used to synthesize 5-benzyl-furan-2-carbaldehyde, with the exception that TPP and Pd(OAc)2 were dissolved in 2:1 CH3CN/isopropyl alcohol. Purification by flash chromatography yielded 4-benzyl-furan-2-carbaldehyde as a white solid (300 mg, 41%). 1H NMR (400 MHz, CDCl3) δ ppm 9.56 (s, 1 H) 7.29-7.38 (m, 3 H) 7.24-7.28 (m, 2 H) 7.17 (d, J=3.5 Hz, 1 H) 6.19 (d, J=3.6 Hz, 1 H) 4.07 (s, 2 H).

後処理

  1. customPurification by flash chromatography

出典と根拠

ORDレコード
ord-38e9e691354f4cd9a9ea970ac403aada
出典データセット
uspto-grants-2009_08
特許番号
US07579370B2

関連ノート

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