(R)-1,5-dimethyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2, 6'(1H,3'H)-dione

Base Information

Chemical Name:(R)-1,5-dimethyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2, 6'(1H,3'H)-dione
CAS No.:1332645-64-3
Molecular Formula:C₂₁H₁₉NO₄
Molecular Weight:349.386
Hs Code.:

Synonyms:(R)-1,5-dimethyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2, 6'(1H,3'H)-dione

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Chemical Property of (R)-1,5-dimethyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2, 6'(1H,3'H)-dione

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Technology Process of (R)-1,5-dimethyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2, 6'(1H,3'H)-dione

There total 5 articles about (R)-1,5-dimethyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2, 6'(1H,3'H)-dione 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: 72.0%

: 66440-60-6
1,5-dimethyl-1H-indole-2,3-dione

: C₁₁H₁₁BrO₂

: 1332645-64-3
(R)-1,5-dimethyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2, 6'(1H,3'H)-dione

Guidance literature:: With 5a(R),10b(S)-5a,10b-dihydro-2-(pentafluorophenyl)-4H,6H-indeno[2,1-b][1,2,4]triazolo[4,3-d][1,4]oxazinium tetrafluoroborate; potassium carbonate; lanthanum(lll) triflate; In tetrahydrofuran; at 0 ℃; for 45h; stereoselective reaction; Schlenk technique;
DOI:10.1021/ol501224p

Reference yield:

: 66440-60-6
1,5-dimethyl-1H-indole-2,3-dione

: (E)-3-(4-methoxyphenyl)but-2-enoyl chloride

: 1332645-64-3
(R)-1,5-dimethyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2, 6'(1H,3'H)-dione

: (S)-1,5-dimethyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2, 6'(1H,3'H)-dione

Guidance literature:: With BF₄*C₃₃H₄₂N₃OSi⁽¹⁺⁾; caesium carbonate; triethylamine; In tetrahydrofuran; at -20 - 20 ℃; for 20h; optical yield given as %ee; enantioselective reaction; Inert atmosphere;
DOI:10.1002/adsc.201100178

Reference yield:

: 7706-82-3
(E)-ethyl 3-(4-methoxyphenyl)but-2-enoate

: 1332645-64-3
(R)-1,5-dimethyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2, 6'(1H,3'H)-dione

: (S)-1,5-dimethyl-4'-(4-methoxyphenyl)spiro[indoline-3,2'-pyran]-2, 6'(1H,3'H)-dione

Guidance literature:: Multi-step reaction with 3 steps

1: water; potassium hydroxide / 100 °C / Inert atmosphere

2: oxalyl dichloride; N,N-dimethyl-formamide / 5 h / 0 - 20 °C / Inert atmosphere

3: BF₄*C₃₃H₄₂N₃OSi⁽¹⁺⁾; caesium carbonate; triethylamine / tetrahydrofuran / 20 h / -20 - 20 °C / Inert atmosphere

With oxalyl dichloride; BF₄*C₃₃H₄₂N₃OSi⁽¹⁺⁾; water; caesium carbonate; triethylamine; N,N-dimethyl-formamide; potassium hydroxide; In tetrahydrofuran;
DOI:10.1002/adsc.201100178