1H-Indole-6-methanol,4-methoxy-(9CI)

Base Information

• Chemical Name: 1H-Indole-6-methanol,4-methoxy-(9CI)
• CAS No.: 791807-50-6
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.203
• Mol file: 791807-50-6.mol

Synonyms:1H-Indole-6-methanol,4-methoxy-(9CI)

Chemical Property of 1H-Indole-6-methanol,4-methoxy-(9CI)

Chemical Property:

• PSA: 45.25000
• LogP: 1.66880

Purity/Quality:

98% ^*data from raw suppliers

4-methoxy-1H-Indole-6-methanol 97.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Indole-6-methanol,4-methoxy-(9CI)

There total 1 articles about 1H-Indole-6-methanol,4-methoxy-(9CI) 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: 93.0%

4-methoxy-1H-indole-6-carboxylic acid methyl ester (41082-79-5) → (4-methoxy-1H-indol-6-yl)methanol (791807-50-6)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 20 ℃; for 2h;

DOI:10.1021/jo040211c

Reference yield:

(4-methoxy-1H-indol-6-yl)methanol (791807-50-6) → 9-methyl-8-methoxy-[(1S,2S)-1,2-(N-tritylaziridino)]-2,3-dihydro-1H-pyrrolo[1,2-a]indole-6-carbaldehyde

Guidance literature:

Multi-step reaction with 12 steps

1.1: 98 percent / NaH / tetrahydrofuran / 1 h / 20 °C

2.1: 82 percent / N-bromosuccinimide / tetrahydrofuran / -78 - 20 °C

3.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

3.2: 92 percent / diethyl ether; pentane / 1 h / -78 - 20 °C

4.1: 85 percent / K₂CO₃ / ethanol; tetrahydrofuran; H₂O / 23 h / 20 °C

5.1: 85 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

6.1: 76 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

7.1: CH₂Cl₂ / Heating

8.1: 98 mg / LiAlH₄ / diethyl ether / 2 h / 0 °C

9.1: CH₂Cl₂ / 0.5 h / -78 °C

10.1: Et₃N / CH₂Cl₂ / -78 - 0 °C

10.2: 28 mg / CH₂Cl₂; acetonitrile / 6 h / 20 °C

11.1: methanesulfonic acid; triisopropylsilane / CH₂Cl₂ / 0.17 h / -42 °C

11.2: 65 percent / (i-Pr)2NEt / CH₂Cl₂ / -42 - 20 °C

With N-Bromosuccinimide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; methanesulfonic acid; chlorotriisopropylsilane; 4 A molecular sieve; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; triethylamine; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; pentane;

DOI:10.1021/jo040211c

Reference yield:

(4-methoxy-1H-indol-6-yl)methanol (791807-50-6) → 9-hydroxymethyl-8-methoxy-[(1S,2S)-1,2-(N-tritylaziridino)]-2,3-dihydro-1H-pyrrolo[1,2-a]indole-6-carboxaldehyde (791807-46-0)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 98 percent / NaH / tetrahydrofuran / 1 h / 20 °C

2.1: 82 percent / N-bromosuccinimide / tetrahydrofuran / -78 - 20 °C

3.1: t-BuLi / diethyl ether; pentane / 0.25 h / -78 °C

3.2: 92 percent / diethyl ether; pentane / 1 h / -78 - 20 °C

4.1: 85 percent / K₂CO₃ / ethanol; tetrahydrofuran; H₂O / 23 h / 20 °C

5.1: 85 percent / TBAF / tetrahydrofuran / 1 h / 0 °C

6.1: 76 percent / tetrapropylammonium perruthenate; 4-methylmorpholine N-oxide; 4 Angstroem molecular sieves / CH₂Cl₂ / 1 h / 20 °C

7.1: CH₂Cl₂ / Heating

8.1: 98 mg / LiAlH₄ / diethyl ether / 2 h / 0 °C

With N-Bromosuccinimide; lithium aluminium tetrahydride; tetrapropylammonium perruthennate; 4 A molecular sieve; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium hydride; potassium carbonate; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; ethanol; dichloromethane; water; pentane;

DOI:10.1021/jo040211c

upstream raw materials:

4-methoxy-1H-indole-6-carboxylic acid methyl ester

Downstream raw materials:

9-hydroxymethyl-8-methoxy-[(1S,2S)-1,2-(N-tritylaziridino)]-2,3-dihydro-1H-pyrrolo[1,2-a]indole-6-carboxaldehyde

6-formyl-8-methoxy-[(1S,2S)-1,2-(N-tritylaziridino)]-2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxylic acid ethyl ester

6-formyl-8-methoxy-[(1S,2S)-1,2-(N-tritylaziridino)]-2,3-dihydro-1H-pyrrolo[1,2-a]indol-9-yl carbamate

6-hydroxymethyl-8-methoxy-[(1S,2S)-1,2-(N-tritylaziridino)]-2,3-dihydro-1H-pyrrolo[1,2-a]indole-9-carboxylic acid ethyl ester

Refernces