Dimethylformamide → 2-(Hydroxymethyl)-2,3-dihydro-1H-indene-5-carbonitrile

HRID 1466039ノート

反応式

HRID 1466039 の反応式
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([CH2:11][OH:12])[CH2:5]2.[CH3:13][N:14](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[OH:12][CH2:11][CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:13]#[N:14])[CH:3]=2)[CH2:7]1

参加物

5

反応物 2

HCID 6228DimethylformamideHCID 68507961(5-Bromo-2,3-dihydro-1H-inden-2-yl)methanol

生成物 1

HCID 685123302-(Hydroxymethyl)-2,3-dihydro-1H-indene-5-carbonitrile

試薬・触媒・溶媒 2

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 178418397HCID 178418397、化合物触媒

反応条件

温度
110 °C

実験手順

A mixture of (5-Bromo-2,3-dihydro-1H-inden-2-yl)methanol (10 g, 44 mmol), Zn(CN)2 (10.3 g, 88 mmol) and Pd(PPh3)4 (1 g, 0.88 mmol) in 100 mL of DMF was heated at 100-120° C. under N2 atmosphere overnight. Most of the solvent was concentrated and the residue was partitioned between water (100 mL) and EtOAc (100 mL) and separated. The aqueous layer was extracted with EtOAc (50 mL×2). The combined organic layers were washed with brine (200 mL), dried over Na2SO4 and concentrated to dryness. The residue was purified with column chromatography (EtOAc/PE=1:20) to give the title compound. 1H-NMR (400 MHz, CDCl3) δ 7.45 (s, 1H), 7.41 (d, J=7.6 Hz, 1H), 7.27 (d, J=8.0 Hz, 1H), 3.64 (d, J=6.6 Hz, 2H), 3.05-3.13 (m, 2H), 2.70-2.84 (m, 3H).

後処理

  1. concentrationMost of the solvent was concentrated
  2. customthe residue was partitioned between water (100 mL) and EtOAc (100 mL)
  3. customseparated
  4. extractionThe aqueous layer was extracted with EtOAc (50 mL×2)
  5. washThe combined organic layers were washed with brine (200 mL)
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated to dryness
  8. customThe residue was purified with column chromatography (EtOAc/PE=1:20)

出典と根拠

ORDレコード
ord-badcbf6fedf94e698f285b18c23b2583
出典データセット
uspto-grants-2015_04
特許番号
US08999990B2

反応ノート

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