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

HRID 1466039노트

반응식

HRID 1466039 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 178418397HCID 178418397, 화합물촉매

반응 조건

온도
110 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-badcbf6fedf94e698f285b18c23b2583
출처 데이터셋
uspto-grants-2015_04
특허 번호
US08999990B2

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