Cyclopentanol → 2-Cyclopentyloxy-4-methoxy-benzonitrile

HRID 1582480노트

반응식

HRID 1582480 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 227211652-Cyclopentyloxy-4-methoxy-benzonitrile수율 95.9%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-e66ebacc89a543a9934e553575281a43
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734302B2

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