δ-diphenylphosphorylbutyl alcohol

Base Information

• Chemical Name: δ-diphenylphosphorylbutyl alcohol
• CAS No.: 891-97-4
• Molecular Formula: C₁₆H₁₉O₂P
• Molecular Weight: 274.299
• Mol file: 891-97-4.mol

Synonyms:δ-diphenylphosphorylbutyl alcohol

Chemical Property of δ-diphenylphosphorylbutyl alcohol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of δ-diphenylphosphorylbutyl alcohol

There total 9 articles about δ-diphenylphosphorylbutyl alcohol 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%

Methyl 4-diphenylphosphinoylbutanoate (114856-27-8) → δ-diphenylphosphorylbutyl alcohol (891-97-4)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; for 4h;

Reference yield:

(3-butenyl)diphenylphosphine-borane complex (127686-64-0) → δ-diphenylphosphorylbutyl alcohol (891-97-4) + (4-diphenylphosphinoyl)-2-butanol (101680-86-8)

Guidance literature:

(3-butenyl)diphenylphosphine-borane complex; With trifluorormethanesulfonic acid; In chloroform-d1; at 0 ℃;

With sodium hydroxide; dihydrogen peroxide; In methanol; Title compound not separated from byproducts;

DOI:10.1021/ja034655m

Reference yield:

diphenylphosphane (829-85-6) → δ-diphenylphosphorylbutyl alcohol (891-97-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / hexane; tetrahydrofuran / 0.5 h / 0 °C

2.1: 2.477 g / borane-tetrahydrofurane complex / hexane; tetrahydrofuran / 0 - 20 °C

3.1: trifluoromethanesulfonic acid / CH₂Cl₂

3.2: H₂O₂; NaOH / methanol

With n-butyllithium; borane-THF; trifluorormethanesulfonic acid; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/jo040125c

upstream raw materials:

Methyl 4-diphenylphosphinoylbutanoate

4-iodobutyl acetate

triphenylphosphine

(3-butenyl)diphenylphosphine-borane complex

Downstream raw materials:

(R)-5-[(R)-1-(Diphenyl-phosphinoyl)-4-hydroxy-butyl]-dihydro-furan-2-one

(S)-5-[(R)-1-(Diphenyl-phosphinoyl)-4-hydroxy-butyl]-dihydro-furan-2-one

6-(Diphenyl-phosphinoyl)-9-hydroxy-5-oxo-nonanoic acid methyl ester

6-(Diphenyl-phosphinoyl)-5,9-dihydroxy-nonanoic acid methyl ester

Refernces

• 1、 Scheideman, Matthew,Shapland, Peter,Vedejs, Edwin. "A mechanistic alternative for the intramolecular hydroboration of homoallylic amine and phosphine borane complexes". . p. 10502 - 10503. Retrieved 2007/10/03.
• 2、 Ayrey, Peter M.,Bolton, Michael A.,Buss, Antony D.,Greeves, Nicholas,Levin, Daniel,et al.. "Stereochemically controlled Synthesis of Unsaturated Alcohols by the Horner-Wittig Reaction". . p. 3407 - 3418. Retrieved 2007/10/02.