4-(tert-butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid 1-methyl-but-3-enyl ester

Base Information

• Chemical Name: 4-(tert-butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid 1-methyl-but-3-enyl ester
• CAS No.: 936913-81-4
• Molecular Formula: C₂₉H₃₃ClO₄Si
• Molecular Weight: 509.117
• Mol file: 936913-81-4.mol

Synonyms:4-(tert-butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid 1-methyl-but-3-enyl ester

Chemical Property of 4-(tert-butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid 1-methyl-but-3-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(tert-butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid 1-methyl-but-3-enyl ester

There total 1 articles about 4-(tert-butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid 1-methyl-but-3-enyl ester 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: 75.0%

(R)-pent-4-en-2-ol (64584-92-5) + 4-tert-butyldiphenylsiloxy-2-chloromethyl-6-hydroxybenzoic acid (378749-93-0) → 4-(tert-butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid 1-methyl-but-3-enyl ester (936913-81-4)

Guidance literature:

With di-isopropyl azodicarboxylate; (2-furyl)phosphine; In benzene; for 12h;

DOI:10.1002/anie.200600593

Reference yield: 100.0%

4-(tert-butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid 1-methyl-but-3-enyl ester (936913-81-4) → 2-chloromethyl-4,6-dihydroxy-benzoic acid 1-methyl-but-3-enyl ester (906374-53-6)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 23 ℃; for 0.5h;

DOI:10.1002/anie.200600593

Reference yield:

4-(tert-butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid 1-methyl-but-3-enyl ester (936913-81-4) → 16,18-bis-ethoxymethoxy-12-methyl-2-phenylselanyl-7,13-dioxa-tricyclo[13.4.0.06,8]nonadeca-1(19),9,15,17-tetraen-14-one

Guidance literature:

Multi-step reaction with 5 steps

1.1: 100 percent / TBAF / tetrahydrofuran / 0.5 h / 23 °C

2.1: (Merrifield resin)-O-(m-C₆H₄SH); i-Pr₂NEt / dimethylformamide / 60 °C

2.2: tetrabutylammonium iodide; 1,8-diazabicyclo[5.4.0]undec-7-ene / dimethylformamide / 20 °C

2.3: 2,2'-azobisisobutyronitrile; n-Bu₃SnH / dimethylformamide / 0.17 h / 150 °C / microwave irradiation

3.1: lithium diisopropylamide / tetrahydrofuran / -78 °C

3.2: 75 percent / tetrahydrofuran / 2 h

4.1: 74 percent / hexamethylphosphoric triamide; lithium diisopropylamide / tetrahydrofuran / -78 °C

5.1: 90 percent / second generation Grubbs catalyst / toluene / 80 °C

With N,N,N,N,N,N-hexamethylphosphoric triamide; (Merrifield resin)-O-(m-C₆H₄SH); tetrabutyl ammonium fluoride; N-ethyl-N,N-diisopropylamine; lithium diisopropyl amide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1002/anie.200600593

upstream raw materials:

(R)-pent-4-en-2-ol

4-tert-butyldiphenylsiloxy-2-chloromethyl-6-hydroxybenzoic acid

Downstream raw materials:

2-chloromethyl-4,6-dihydroxy-benzoic acid 1-methyl-but-3-enyl ester

2,4-bis-ethoxymethoxy-6-methyl-benzoic acid 1-methyl-but-3-enyl ester

2,4-bis-ethoxymethoxy-6-phenylselanylmethyl-benzoic acid 1-methyl-but-3-enyl ester

11-benzyloxy-2-ethoxymethoxy-4,12-dihydroxy-7-methyl-7,8,11,12,13,14-hexahydro-6-oxa-benzocyclotetradecen-5-one