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

HRID 2173256ノート

反応式

HRID 2173256 の反応式
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

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 11186Zinc cyanide (Zn(CN)2)触媒HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-74a2ab077706474a9f188b275b8fb0f3
出典データセット
uspto-grants-2015_06
特許番号
US09056859B2

反応ノート

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