1-[5-benzyloxymethyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrol-3-yl]-ethanone

Base Information

Chemical Name:1-[5-benzyloxymethyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrol-3-yl]-ethanone
CAS No.:536744-95-3
Molecular Formula:C₂₃H₂₅NO₄S
Molecular Weight:411.522
Hs Code.:

1-[5-benzyloxymethyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1<i>H</i>-pyrrol-3-yl]-ethanone

Synonyms:1-[5-benzyloxymethyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrol-3-yl]-ethanone

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Chemical Property of 1-[5-benzyloxymethyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrol-3-yl]-ethanone

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Technology Process of 1-[5-benzyloxymethyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrol-3-yl]-ethanone

There total 6 articles about 1-[5-benzyloxymethyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrol-3-yl]-ethanone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

: 536744-94-2
N-1-[benzyloxymethyl-4-(tertbutyldimethylsilanoxy)but-2-ynyl]-N-but-2-ynyl-4-methylbenzenesulfonamide

: 536744-95-3
1-[5-benzyloxymethyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrol-3-yl]-ethanone

Guidance literature:: With cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; malonic acid; In water; acetone; at 40 ℃; for 3h;
DOI:10.1021/ol034241y

Reference yield:

: 60656-87-3
benzyloxyacetoaldehyde

: 536744-95-3
1-[5-benzyloxymethyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrol-3-yl]-ethanone

Guidance literature:: Multi-step reaction with 5 steps

1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

1.2: 99 percent / tetrahydrofuran / 3.5 h / -78 - -40 °C

2.1: 99 percent / TEMPO; NaOCl; NaHCO₃ / KBr / CH₂Cl₂; H₂O / 1.5 h

3.1: 93 percent / LiAlH₄; (R)-BINOL; methanol / tetrahydrofuran / 3.25 h / -100 - -78 °C

4.1: 86 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 48 h / 20 °C

5.1: 80 percent / [CpRu(CH₃CN)3]PF₆; malonic acid / acetone; H₂O / 3 h / 40 °C

With methanol; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; lithium aluminium tetrahydride; n-butyllithium; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; malonic acid; di-isopropyl azodicarboxylate; (R)-1,1'-Bi-2-naphthol; sodium hydrogencarbonate; triphenylphosphine; potassium bromide; In tetrahydrofuran; dichloromethane; water; acetone; 4.1: Mitsunobu reaction;
DOI:10.1021/ol034241y

Reference yield:

: 536744-92-0
1-benzyloxy-5-(tert-butyldimethylsilanyloxy)pent-3-yn-2-ol

: 536744-95-3
1-[5-benzyloxymethyl-1-(toluene-4-sulfonyl)-4-vinyl-2,5-dihydro-1H-pyrrol-3-yl]-ethanone

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / TEMPO; NaOCl; NaHCO₃ / KBr / CH₂Cl₂; H₂O / 1.5 h

2: 93 percent / LiAlH₄; (R)-BINOL; methanol / tetrahydrofuran / 3.25 h / -100 - -78 °C

3: 86 percent / triphenylphosphine; diisopropyl azodicarboxylate / tetrahydrofuran / 48 h / 20 °C

4: 80 percent / [CpRu(CH₃CN)3]PF₆; malonic acid / acetone; H₂O / 3 h / 40 °C

With methanol; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; lithium aluminium tetrahydride; cyclopentadienylruthenium(II) trisacetonitrile hexafluorophosphate; malonic acid; di-isopropyl azodicarboxylate; (R)-1,1'-Bi-2-naphthol; sodium hydrogencarbonate; triphenylphosphine; potassium bromide; In tetrahydrofuran; dichloromethane; water; acetone; 3: Mitsunobu reaction;
DOI:10.1021/ol034241y