Cyclopentanol → 2-Cyclopentyloxy-4-methoxy-benzonitrile

HRID 1167314ノート

反応式

HRID 1167314 の反応式
[OH:1][C:2]1[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH:12]1(O)[CH2:16][CH2:15][CH2:14][CH2:13]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1>[CH:12]1([O:1][C:2]2[CH:9]=[C:8]([O:10][CH3:11])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])[CH2:16][CH2:15][CH2:14][CH2:13]1

参加物

5

反応物 3

HCID 7298CyclopentanolHCID 11776TriphenylphosphineHCID 114236802-Hydroxy-4-methoxybenzonitrile

生成物 1

HCID 227211652-Cyclopentyloxy-4-methoxy-benzonitrile収率 100.4%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 2-hydroxy-4-methoxy-benzonitrile (90 mg, 0.573 mmol), cyclopentanol (55 mg, 0.630 mmol) and triphenylphosphine (167 mg, 0.630 mmol) in tetrahydrofuran (3 mL) cooled to −78° was added diethylazodicarboxalate (0.16 mL, 0.860 mmol). The cooling bath was removed and the reaction was allowed to warm up to room temperature over 1.5 h. The reaction mixture was concentrated in vacuo, and purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 0-8% diethyl ether in hexanes yielded 2-cyclopentyloxy-4-methoxy-benzonitrile as a clear liquid (125 mg, 96%).

後処理

  1. additionwas added diethylazodicarboxalate (0.16 mL, 0.860 mmol)
  2. customThe cooling bath was removed
  3. concentrationThe reaction mixture was concentrated in vacuo, and purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  4. washeluting with 0-8% diethyl ether in hexanes

出典と根拠

ORDレコード
ord-89c21a658c1942c593f40916d60090c0
出典データセット
uspto-grants-2003_09
特許番号
US06617346B1

反応ノート

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