ethyl 1-benzyloxymethyl-5-bromo-2-methoxymethyl-1H-pyrrol-3-carboxylate → Ethyl 1-benzyloxymethyl-5-bromo-2-formyl-1H-pyrrol-3-carboxylate

HRID 2097490Notes

Reaction equation

HRID 2097490 reaction equation
[CH2:1]([O:8][CH2:9][N:10]1[C:14]([Br:15])=[CH:13][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:11]1[CH2:21][O:22]C)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.BrC1N(COCC[Si](C)(C)C)C(COC)=C(C(OCC)=O)C=1>>[CH2:1]([O:8][CH2:9][N:10]1[C:14]([Br:15])=[CH:13][C:12]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:11]1[CH:21]=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 66602530ethyl 1-benzyloxymethyl-5-bromo-2-methoxymethyl-1H-pyrrol-3-carboxylateHCID 66602785ethyl 5-bromo-2-methoxymethyl-1-(2-trimethylsilylethoxymethyl)-1H-pyrrol-3-carboxylate

Product 1

HCID 86627040Ethyl 1-benzyloxymethyl-5-bromo-2-formyl-1H-pyrrol-3-carboxylateYield 95%

Procedure

Reaction and post treatment were carried out in the same manner as in Reference example 15-(f) except for using 895 g (purity: 85.1%, 1.99 mol) of ethyl 1-benzyloxymethyl-5-bromo-2-methoxymethyl-1H-pyrrol-3-carboxylate obtained in Reference example 17-(b) in place of ethyl 5-bromo-2-methoxymethyl-1-(2-trimethylsilylethoxymethyl)-1H-pyrrol-3-carboxylate, whereby 805 g (purity: 86.3%) of the title compound was obtained as a brownish oil. (Yield: 95%)

Workup

  1. customReaction and post treatment

Sources & evidence

ORD record
ord-98204c94ae24416b97d4c7885de83d58
Source dataset
uspto-grants-2013_05
Patent number
US08450319B2

Reaction notes

Loading…