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

HRID 2062051
Notes
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Reaction equation

HRID 2062051 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-0e9a395c2d994fc7ae639b28853098dd
Source dataset
uspto-grants-2012_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08283479B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes