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

HRID 2361298Notes

Reaction equation

HRID 2361298 reaction equation
[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

Participants

7

Reactant 5

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Sources & evidence

ORD record
ord-cbdb16503d674b48af0bbf26dac393a0
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

Loading…