HCID 67657348, compound → HCID 53940374, compound

HRID 326986Notes

Reaction equation

HRID 326986 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-3effeeaadbcc41a5a0a3d13388f53c08
Source dataset
uspto-grants-1993_12
Patent number
US05272134

Reaction notes

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