Triethylamine → Methyl 1-benzyl-4-formyl-5-(3-hydroxy-3,3-diphenylprop-1-ynyl)-1H-pyrrole-2-carboxylate

HRID 1952514ノート

反応式

HRID 1952514 の反応式
[CH2:1]([N:8]1[C:12](I)=[C:11]([CH:14]=[O:15])[CH:10]=[C:9]1[C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]1([C:26]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([OH:29])[C:27]#[CH:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCN(CC)CC>CN(C=O)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([N:8]1[C:12]([C:28]#[C:27][C:26]([OH:29])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[C:11]([CH:14]=[O:15])[CH:10]=[C:9]1[C:16]([O:18][CH3:19])=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

8

反応物 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 92976DiphenylethynylcarbinolHCID 86664847Methyl 1-benzyl-4-formyl-5-iodo-1H-pyrrole-2-carboxylate

生成物 1

HCID 86664849Methyl 1-benzyl-4-formyl-5-(3-hydroxy-3,3-diphenylprop-1-ynyl)-1H-pyrrole-2-carboxylate収率 87%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒

実験手順

A solution of 5 (0.47 g, 1.3 mmol), 1,1-diphenylprop-2-yn-1-ol (0.66 g, 3.2 mmol), CuI (0.05 g, 0.3 mmol), Pd(PPh3)2Cl2 (0.18 g, 0.3 mmol), PPh3 (0.07 g, 0.3 mmol), and Et3N (4 mL) in anhydrous DMF (4 mL) was stirred for 16 hours at 70° C. under N2 atmosphere. The reaction mixture was partitioned between water and EtOAc. The combined organic layer was dried over MgSO4, filtered and concentrated in vacuo. MPLC purification (Hexanes:EtOAc/80:20) of the residue gave 6 as a pale yellow solid (0.49 g, 87%). 1H NMR (400 MHz, CDCl3) δ 9.88 (s, 1H), 7.50-7.52 (m, 4H), 7.36 (s, 1H), 7.24-7.30 (m, 8H), 7.04 (m, 2H), 5.69 (s, 2H), 3.80 (s, 3H), and 3.65 (s, 1H); 13C NMR (100 MHz, CDCl3) δ 185.16, 160.72, 144.07, 136.84, 128.91, 128.72, 128.33, 127.91, 127.79, 127.05, 126.23, 124.96, 116.97, 103.35, 75.37, 75.27, 52.15, and 50.38.

後処理

  1. customThe reaction mixture was partitioned between water and EtOAc
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customMPLC purification (Hexanes:EtOAc/80:20) of the residue

出典と根拠

ORDレコード
ord-6d558603bef5427ba7f75ce064131679
出典データセット
uspto-grants-2013_03
特許番号
US08404728B2

反応ノート

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