Water → 6-Methoxy-3,3-dimethyl-5-prop-2-ynyloxy-indan-1-one

HRID 2228351Notes

Reaction equation

HRID 2228351 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:14])([CH3:13])[CH2:8][C:9]2=[O:12])=[CH:5][C:4]=1[OH:15].[CH2:16](Br)[C:17]#[CH:18].C([O-])([O-])=O.[K+].[K+].O>CN1CCCC1=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH3:13])([CH3:14])[CH2:8][C:9]2=[O:12])=[CH:5][C:4]=1[O:15][CH2:18][C:17]#[CH:16]

Participants

7

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 134808615-Hydroxy-6-methoxy-3,3-dimethyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 184695826-Methoxy-3,3-dimethyl-5-prop-2-ynyloxy-indan-1-oneYield 103.6%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

6-Methoxy-3,3-dimethyl-5-hydroxy-indan-1-one (2.2 g), 1.5 g of propargyl bromide, and 3.7 g of K2CO3 in 9 ml of 1-methyl pyrrolidone was placed in a 25 ml reaction flask and stirred for one hour. Then, it was stirred further at 100° C. for one hour. The reaction mixture was distributed between water and ethyl acetate. The organic phase was washed with 1N NaOH solution and NaCl solution, dried over Na2SO4 and concentrated to yield 2.7 g of a yellow liquid. UV 310 nm (ε=18′734), MS: 244(M+), 229, 105(100%).

Workup

  1. stirringThen, it was stirred further at 100° C. for one hour
  2. washThe organic phase was washed with 1N NaOH solution and NaCl solution
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-907eb91c0e7041108994571340472b5c
Source dataset
uspto-grants-2002_07
Patent number
US06416746B1

Reaction notes

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