Acetic Anhydride → 5-Benzyloxyindole

HRID 1246941Notes

Reaction equation

HRID 1246941 reaction equation
OCC[N:4]1[C:12]2[C:7](=[CH:8][C:9]([O:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.C(OC(=O)C)(=O)C.C(N(CC)CC)C>CN(C1C=CN=CC=1)C.C1COCC1>[CH2:14]([O:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][CH:5]=[CH:6]2)[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 21906934HCID 21906934, compound

Product 1

HCID 146245-BenzyloxyindoleYield 138.3%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Crude N-(2-hydroxyethyl)-5-benzyloxyindole (11.09 g, 42.1 mmol), acetic anhydride (4.36 mL, 46.3 mmol), triethylamine (6.50 mL,46.3 mmol), and DMAP (100 mg) were stirred together in THF for 1 hour before standard aqueous workup provided N-2-acetoxyethyl)-5-benzyloxyindole as a clear oil (13.0 g, 99%). 1H NMR (500 MHz, CDCl3) δ 7.51 (d, J=8.1 Hz, 2H), 7.42 (t, J=8.1 Hz, 2H), 7.35 (s, 1H), 7.27 (d, J=8.9 Hz, 1H), 7.21 (d, J=2.4 Hz, 1H), 7.09 (d, J=3.1 Hz, 1H), 7.01 (dd, J=2.4, 8.1 Hz, 1H), 6.47 (dd, J=0.8, 3.1 Hz, 1H),5.14(s,2H), 4.37 (t, J=5.0 Hz 2H), 4.31(t, J=5.0 Hz, 2H), 2.02 (s, 3H).

Sources & evidence

ORD record
ord-da4e5030fbaf4fd4a580536af6355c4f
Source dataset
uspto-grants-2006_10
Patent number
US07129250B2

Reaction notes

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