Ethyl 3-(3-bromophenyl)acrylate → 3-[3-(3-Thienyl)phenyl]-1-propanol

HRID 1464762Notes

Reaction equation

HRID 1464762 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[S:7]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]([CH:22]=[CH:23][CH:24]=2)/[CH:15]=[CH:16]/[C:17](OCC)=[O:18])=[CH:8]1.BrC1C=C(C=CC=1)/C=C/C(OCC)=O.C([Sn](CCCC)(CCCC)C1C=CSC=1)CCC>O1CCCC1>[S:7]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[C:14]([CH2:15][CH2:16][CH2:17][OH:18])[CH:22]=[CH:23][CH:24]=2)=[CH:8]1

Participants

6

Reactant 4

HCID 5369361Ethyl 3-(3-bromophenyl)acrylateHCID 10959689Stannane, tributyl-3-thienyl-HCID 21226445Aluminium lithium hydrideHCID 86747788ethyl (E)-3-(3-thienyl)cinnamate

Product 1

HCID 199170763-[3-(3-Thienyl)phenyl]-1-propanolYield 62%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension (20 ml) of 0.4 g of lithium aluminum hydride in terahydrofuran was added, under ice cooling, a tetrahydrofuran solution (10 ml) of 2.1 g of ethyl (E)-3-(3-thienyl)cinnamate [synthesized by the same reaction as in Referential Example 12 using ethyl (E)-3-bromocinnamate [see Org. Syn. I, 252] and tri-n-butyl(3-thienyl)tin ]. The mixture was stirred at room temperature for 30 minutes, and then refluxed for 30 minutes. The solution was worked up in a customary manner, and the product was purified by medium-pressure liquid chromatography [silica gel column, hexane/ethyl acetate=5/1→5/2] to give 1.1 g of 3-[3-(3-thienyl)phenyl]-1-propanol as a pale yellow oil.

Workup

  1. temperaturerefluxed for 30 minutes
  2. customthe product was purified by medium-pressure liquid chromatography [silica gel column, hexane/ethyl acetate=5/1→5/2]

Sources & evidence

ORD record
ord-cd9f8c5d1a364f1eba4fe29d9b2e2759
Source dataset
uspto-grants-1994_04
Patent number
US05306728

Reaction notes

Loading…