Acetyl chloride → [5-(Benzyloxy)-1H-indol-2-yl]methyl acetate

HRID 2212161Notes

Reaction equation

HRID 2212161 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]([CH2:18][OH:19])=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20](Cl)(=[O:22])[CH3:21]>>[C:20]([O:19][CH2:18][C:13]1[NH:14][C:15]2[C:11]([CH:12]=1)=[CH:10][C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[CH:17][CH:16]=2)(=[O:22])[CH3:21]

Participants

3

Reactant 2

HCID 6367Acetyl chlorideHCID 10682298[5-(Benzyloxy)-1H-indol-2-yl]methanol

Product 1

HCID 21964292[5-(Benzyloxy)-1H-indol-2-yl]methyl acetate

Procedure

The title compound was prepared from [5-(benzyloxy)-1H-indol-2-yl]methanol and acetyl chloride in substantially the same manner, as described in step 4 of Example 1. The product was obtained as a gray solid. Mass spectrum (ESI, [M+H]+) m/z 296. 1H NMR (400 MHz, DMSO-d6) δ 11.03 (s, 1H), 7.45 (d, 2H, J=7.33 Hz), 7.38 (t, 2H, J=7.49 Hz), 7.30 (d, 1H, J=7.20 Hz), 7.24 (d, 1H, J=8.71 Hz), 7.08 (s, 1H), 6.81 (dd, 1H, J=8.70 and 1.45 Hz), 6.34 (s, 1H), 5.13 (s, 2H), 5.06 (s, 2H), 2.04 ppm (s, 3H).

Workup

  1. customThe product was obtained as a gray solid

Sources & evidence

ORD record
ord-fdba74e82ea94073befa8cf943aae4ae
Source dataset
uspto-grants-2006_09
Patent number
US07101903B2

Reaction notes

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