Cyclopentanol → 2-Cyclopentyloxy-4-methoxy-benzonitrile

HRID 1167314노트

반응식

HRID 1167314 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>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

참가 물질

5

반응물 3

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

생성물 1

HCID 227211652-Cyclopentyloxy-4-methoxy-benzonitrile수율 100.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-89c21a658c1942c593f40916d60090c0
출처 데이터셋
uspto-grants-2003_09
특허 번호
US06617346B1

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