Sodium hydride → (E)-3-(1-phenylmethanesulfonyl-1H-pyrrol-3-yl)-acrylic acid tert-butylester

HRID 1948644Notes

Reaction equation

HRID 1948644 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:16])/[CH:9]=[CH:10]/[C:11]1[CH:15]=[CH:14][NH:13][CH:12]=1)([CH3:6])([CH3:5])[CH3:4].[C:17]1([CH2:23][S:24](Cl)(=[O:26])=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>>[C:3]([O:7][C:8](=[O:16])/[CH:9]=[CH:10]/[C:11]1[CH:15]=[CH:14][N:13]([S:24]([CH2:23][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)(=[O:26])=[O:25])[CH:12]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 74740Phenylmethanesulfonyl chlorideHCID 66646340tert-butyl (2E)-3-(1H-pyrrol-3-yl)prop-2-enoate2×

Product 1

HCID 66646367(E)-3-(1-phenylmethanesulfonyl-1H-pyrrol-3-yl)-acrylic acid tert-butylester

Procedure

Starting materials: sodium hydride 60% (0.240 g), (E)-3-(1H-pyrrol-3-yl)-acrylic acid tert-butyl ester (compound D1) (1.01 g), α-toluenesulfonylchloride (1.19 g). Reaction conditions: −30° C., 30 min; 30° C., 2.5 hours.

Workup

  1. customReaction conditions
  2. custom−30° C., 30 min
  3. custom30° C., 2.5 hours

Sources & evidence

ORD record
ord-e6742470f1424c93ac7086bedb8e9c87
Source dataset
uspto-grants-2013_03
Patent number
US08399505B2

Reaction notes

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