HCID 67657348, compound → HCID 53940374, compound

HRID 1197756Notes

Reaction equation

HRID 1197756 reaction equation
S(NN=[C:13]1[CH2:18][CH2:17][C@H:16]2[C@H:19]3[C@H:30]([CH2:31][CH2:32][C@:14]12[CH3:15])[C@:27]1([CH2:28][OH:29])[C:22](=[CH:23][CH:24]([OH:33])[CH2:25][CH2:26]1)[CH2:21][CH2:20]3)(C1C=CC(C)=CC=1)(=O)=O.C([Li])CCC>O1CCCC1.CCCCCC>[OH:33][CH:24]1[CH2:25][CH2:26][C@@:27]2([CH2:28][OH:29])[C:22]([CH2:21][CH2:20][C@@H:19]3[C@@H:30]2[CH2:31][CH2:32][C@@:14]2([CH3:15])[C@H:16]3[CH2:17][CH:18]=[CH:13]2)=[CH:23]1

Participants

5

Reactant 2

HCID 67657348HCID 67657348, compoundHCID 178418339Butyllithium

Product 1

HCID 53940374HCID 53940374, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

The tosylhydrazone (20) in tetrahydrofuran is treated with n-butyl lithium (BuLi, b) in hexane and the mixture is stirred at room temperature for 16 hours. Aqueous work up is followed by extraction and purification to yield the diene (21).

Workup

  1. extractionAqueous work up is followed by extraction and purification

Sources & evidence

ORD record
ord-26f761ea17f2494a831cecccec7fcd10
Source dataset
uspto-grants-1994_01
Patent number
US05278141

Reaction notes

Loading…