1-(3-Chloro-4-methoxyphenyl)-4-methylpent-2-yne-1,4-diol → 1-(3-Chloro-4-methoxyphenyl)-4-hydroxy-4-methylpent-2-yn-1-one

HRID 655459Notes

Reaction equation

HRID 655459 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([OH:17])[C:11]#[C:12][C:13]([CH3:16])([OH:15])[CH3:14])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]>C(Cl)Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:10](=[O:17])[C:11]#[C:12][C:13]([OH:15])([CH3:14])[CH3:16])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9]

Participants

4

Reactant 1

HCID 593547411-(3-Chloro-4-methoxyphenyl)-4-methylpent-2-yne-1,4-diol

Product 1

HCID 593547741-(3-Chloro-4-methoxyphenyl)-4-hydroxy-4-methylpent-2-yn-1-oneYield 65.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 1-(3-chloro-4-methoxyphenyl)-4-methylpent-2-yne-1,4-diol (0.69 g, 2.716 mmol) in DCM (20 mL) was added DMP (2.36 g, 5.430 mmol) at RT. The reaction mixture was stirred for 1 h and diluted with water (10 mL). The combined organic layers were washed with a saturated NaHCO3 solution and water, dried over Na2SO4, filtered, and then concentrated in vacuo to afford 1-(3-chloro-4-methoxyphenyl)-4-hydroxy-4-methylpent-2-yn-1-one (0.45 g, 65%) as a brown oil.

Workup

  1. washThe combined organic layers were washed with a saturated NaHCO3 solution and water
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-81df8a3dfc1c4788ab1ea4cfa683ff39
Source dataset
uspto-grants-2011_12
Patent number
US08071595B2

Reaction notes

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