N,N,N',N'-Tetramethylethylenediamine → 4-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile

HRID 2173256노트

반응식

HRID 2173256 반응식
Br[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[O:10][CH2:9][CH2:8][CH:7]2[CH2:12][OH:13].[CH3:14][N:15](CCN(C)C)C.CCOC(C)=O>CN(C=O)C.[C-]#N.[C-]#N.[Zn+2].C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[OH:13][CH2:12][CH:7]1[C:6]2[C:11](=[C:2]([C:14]#[N:15])[CH:3]=[CH:4][CH:5]=2)[O:10][CH2:9][CH2:8]1

참가 물질

7

반응물 3

HCID 8037N,N,N',N'-TetramethylethylenediamineHCID 8857Ethyl AcetateHCID 67516017(8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol

생성물 1

HCID 675169644-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile

시약·촉매·용매 3

HCID 11186Zinc cyanide (Zn(CN)2)촉매HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 6228Dimethylformamide용매

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온도
100 °C

실험 절차

A solution of (8-bromo-3,4-dihydro-2H-chromen-4-yl)methanol (1 g, 4.12 mmol) in 3 mL of DMF was added Zn(CN)2 (481 mg, 4.12 mmol), Pd2(dba)3 (67 mg, 0.04 mmol), TMEDA (191 mg, 1.6 mmol), Xantphose (48 mg, 0.08 mmol), and the mixture was stirred under microwave irradiation for 5 min at 100° C. The mixture was added with 10 mL of EtOAc, washed with brine, dried over anhydrous Na2SO4 and concentrated. The residue was purified by prep-TLC to give 4-(hydroxymethyl)-3,4-dihydro-2H-chromene-8-carbonitrile.

후처리

  1. washwashed with brine
  2. dry with materialdried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customThe residue was purified by prep-TLC

출처 및 근거

ORD 기록
ord-74a2ab077706474a9f188b275b8fb0f3
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09056859B2

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