Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylate → [5-(Benzyloxy)-1H-indol-2-yl]methanol

HRID 2373487Notes

Reaction equation

HRID 2373487 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([C:18](OCC)=[O:19])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[NH:14][C:13]([CH2:18][OH:19])=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

3

Reactant 2

HCID 95721Ethyl 5-(phenylmethoxy)-1H-indole-2-carboxylateHCID 21226445Aluminium lithium hydride

Product 1

HCID 10682298[5-(Benzyloxy)-1H-indol-2-yl]methanol

Procedure

The title compound was prepared from ethyl 5-(benzyloxy)-1H-indole-2-carboxylate and lithium aluminum hydride according to the procedure described in step 3 of Example 1. The product was obtained as a white solid, mp: 106-107° C. Mass spectrum (ESI, [M+H]+) m/z 254. 1H NMR (400 MHz, DMSO-d6) δ 10.80 (s, 1H), 7.45 (d, 2H, J=7.33 Hz), 7.37 (t, 2H, J=7.49 Hz), 7.30 (d, 1H, J=7.18 Hz), 7.20 (d, 1H, J=8.71 Hz), 7.04 (s, 1H), 6.74 (dd, 1H, J=8.70 and 1.46 Hz), 6.16 (s, 1H), 5.16 (t, 1H, J=5.49 Hz), 5.01 (s, 2H), 4.55 ppm (d, 2H, J=5.50 Hz).

Workup

  1. customThe product was obtained as a white solid, mp: 106-107° C

Sources & evidence

ORD record
ord-59937003a1ef4f5cb86bd01b77ec06a9
Source dataset
uspto-grants-2008_12
Patent number
US07459478B2

Reaction notes

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