Dimethylformamide → 1-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethoxy)-naphthalene-2-carboxylic acid methyl ester

HRID 2075483Notes

Reaction equation

HRID 2075483 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[CH:10][C:9]=1[C:18]([O:20][CH3:21])=[O:19].CN(C=O)C.Br[CH2:28][CH:29]1[O:34][C:33]2[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=2[O:31][CH2:30]1>C(OCC)(=O)C>[CH3:21][O:20][C:18]([C:9]1[CH:10]=[CH:11][C:12]2[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:8]=1[O:7][CH2:28][CH:29]1[O:34][C:33]2[CH:35]=[CH:36][CH:37]=[CH:38][C:32]=2[O:31][CH2:30]1)=[O:19]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 703582-Naphthalenecarboxylic acid, 1-hydroxy-, methyl esterHCID 983332-Bromomethyl-1,4-benzodioxane

Product 1

HCID 667012071-(2,3-Dihydro-benzo[1,4]dioxin-2-ylmethoxy)-naphthalene-2-carboxylic acid methyl esterYield 55.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To 4.19 g cesium carbonate and 1.37 g methyl 1-hydroxy-2-naphthoate in 25 ml abs. DMF was added 1.62 g 2-bromomethyl-2,3-dihydro-benzo[1,4]dioxine and the mixture was reacted for 16 h at 50° C. The reaction was poured unto ice, the resulting precipitate was isolated by filtration, dissolved in ethyl acetate and washed with brine. The organic phase was dried over magnesium sulphate and concentrated in vacuo. The resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate) to yield 1.31 g of 1-(2,3-dihydro-benzo[1,4]dioxin-2-ylmethoxy)-naphthalene-2-carboxylic acid methyl ester.

Workup

  1. customthe mixture was reacted for 16 h at 50° C
  2. additionThe reaction was poured unto ice
  3. customthe resulting precipitate was isolated by filtration
  4. washwashed with brine
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated in vacuo
  7. customThe resulting residue was purified by flash chromatography (silica, heptane/ethyl acetate)

Sources & evidence

ORD record
ord-a66146e51e9440f49a657fc8c977e4ac
Source dataset
uspto-grants-2011_04
Patent number
US07919628B2

Reaction notes

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