Indole → 6-(Tetrahydrofuran-3-yloxy)-1H-indole

HRID 2361298ノート

反応式

HRID 2361298 の反応式
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:10])[CH:8]=2)[CH:3]=[CH:2]1.[O:11]1[CH2:15][CH2:14][CH:13](O)[CH2:12]1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O.N1C2C(=CC=CC=2)C=C1>ClCCl>[O:11]1[CH2:15][CH2:14][CH:13]([O:10][C:7]2[CH:8]=[C:9]3[C:4]([CH:3]=[CH:2][NH:1]3)=[CH:5][CH:6]=2)[CH2:12]1

参加物

7

反応物 5

HCID 798IndoleHCID 99603-Furanol, tetrahydro-HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 5245086-Hydroxyindole

生成物 1

HCID 679946796-(Tetrahydrofuran-3-yloxy)-1H-indole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 1H-indol-6-ol (2.00 g, 15.02 mmol), tetrahydrofuran-3-ol (1.46 mL, 18.0 mmol), and triphenylphosphine (4.33 g, 16.52 mmol) in dichloromethane (80 mL) at 0° C. was added diisopropyl diazene-1,2-dicarboxylate (3.49 mL, 18.03 mmol) over 10 min. The mixture was stirred at room temperature for 16 hr. The starting indole and desired product were detected in a ratio of 3:2. The dark mixture was diluted with CH2Cl2 (80 mL), washed with 1N NaOH (50 mL), water (50 mL), and brine (50 mL). The organic solution was dried over anhydrous MgSO4. The desired product (0.642 g, 3.16 mmol, 21.03% yield) was isolated as viscous oil by ISCO (300 g silica gel, solid loading, 10-50% ethyl acetate/hexane).

出典と根拠

ORDレコード
ord-cbdb16503d674b48af0bbf26dac393a0
出典データセット
uspto-grants-2014_04
特許番号
US08685969B2

反応ノート

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