Epichlorohydrin → 6-Methoxy-5-oxiranylmethoxy-indan-1-one

HRID 460347Notes

Reaction equation

HRID 460347 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][C:10]=1[O:11][CH3:12])[C:7](=[O:13])[CH2:6][CH2:5]2.Cl[CH2:15][CH:16]1[CH2:18][O:17]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.C(OCC)(=O)C>[CH3:12][O:11][C:10]1[CH:9]=[C:8]2[C:4]([CH2:5][CH2:6][C:7]2=[O:13])=[CH:3][C:2]=1[O:1][CH2:15][CH:16]1[CH2:18][O:17]1

Participants

6

Reactant 3

HCID 7835EpichlorohydrinHCID 11430Potassium CarbonateHCID 147633955-Hydroxy-6-methoxy-2,3-dihydro-1H-inden-1-one2×

Product 1

HCID 184458206-Methoxy-5-oxiranylmethoxy-indan-1-one

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-Hydroxy-6-methoxy-indan-1-one (Intermediate H, 5.0 g, 0.028 mole), 2-chloromethyl-oxirane (4.4 mL, 0.056 mole), and potassium carbonate (11.6 g, 0.084 mole) was stirred in 50 mL of DMF at 70° C. overnight under Argon. The reaction was then diluted with 200 mL of ethyl acetate and washed 3 times with water. The ethyl acetate solution was dried over sodium sulfate and the solvent removed in vacuo to yield the title compound (Intermediate M). MS m/z 236 (M+H)+.

Workup

  1. washwashed 3 times with water
  2. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  3. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-ae16e05b17f74960bd248064bdd32235
Source dataset
uspto-grants-2007_03
Patent number
US07196110B2

Reaction notes

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