HCID 59354761, compound → HCID 59354820, compound

HRID 1425811Notes

Reaction equation

HRID 1425811 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:22])[C:16]#[C:17][C:18]([CH3:21])([OH:20])[CH3:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=C[NH+]=CC=1.[O-][Cr](Cl)(=O)=O>C(Cl)Cl>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:22])[C:16]#[C:17][C:18]([OH:20])([CH3:19])[CH3:21])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 59354761HCID 59354761, compoundHCID 178418287HCID 178418287, compound

Product 1

HCID 59354820HCID 59354820, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-(benzyloxy)phenyl)-4-methylpent-2-yne-1,4-diol (3.0 g, 0.01 mol) in DCM (30 mL) were added Celitc® (1.0 g) followed by PCC (2.61 g, 0.01 mol) at RT. The reaction mixture was stirred for 1 h, filtered through a pad of Celite® and the filtrate was concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 1-(4-(benzyloxy)phenyl)-4-hydroxy-4-methylpent-2-yn-1-one (1.5 g, 51%) as a solid.

Workup

  1. filtrationfiltered through a pad of Celite®
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto obtain the crude product
  4. customThe crude material was purified via silica gel column chromatography

Sources & evidence

ORD record
ord-f613883e9fbd48a2ac5e1da7fea109b6
Source dataset
uspto-grants-2015_01
Patent number
US08933074B2

Reaction notes

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