Cyclopentanol → 2-Cyclopentyloxy-4-methoxy-benzonitrile

HRID 1582480ノート

反応式

HRID 1582480 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>C1COCC1>[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 95.9%

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, 0.60 mmol, example 9), cyclopentanol (55 mg, 0.64 mmol) and triphenylphosphine (167 mg, 0.64 mmol) in THF (3 mL) at −78° C. was added diethyl azodicarboxalate (0.16 mL, 0.860 mmol, 85%). 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, 90%).

後処理

  1. customThe cooling bath was removed
  2. 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)
  3. washeluting with 0-8% diethyl ether in hexanes

出典と根拠

ORDレコード
ord-e66ebacc89a543a9934e553575281a43
出典データセット
uspto-grants-2004_05
特許番号
US06734302B2

反応ノート

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