Tetrahydrofuran → Ethyl (5-chloro-1,3-dihydro-2-benzofuran-1-yl)acetate

HRID 2056745Notes

Reaction equation

HRID 2056745 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6](O)[O:7][CH2:8][C:4]=2[CH:3]=1.C(=O)([O-])[O-:13].[Cs+].[Cs+].[CH2:18]1[CH2:22][O:21][CH2:20][CH2:19]1>>[Cl:1][C:2]1[CH:11]=[CH:10][C:5]2[CH:6]([CH2:19][C:20]([O:21][CH2:22][CH3:18])=[O:13])[O:7][CH2:8][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 693101565-Chloro-1,3-dihydroisobenzofuran-1-ol

Product 1

HCID 86592978Ethyl (5-chloro-1,3-dihydro-2-benzofuran-1-yl)acetate

Conditions

Temperature
0 °C

Procedure

5-Chloro-1,3-dihydro-2-benzofuran-1-ol (2.95 g, 17.3 mmol) was dissolved in THF (60 mL) and cooled to 0° C. Triethyl phosphonoacetate (11.7 g, 52.1 mmol) and caesium carbonate (17 g, 52.1 mmol) were added. After 20 min the cold bath was removed and the reaction mixture allowed to stir at room temperature for 3 h, then quenched with a saturated solution of ammonium chloride and extracted with ethyl acetate. The combined organic layers were washed with brine, dried (MgSO4), filtered and evaporated in vacuo. Purification by column chromatography, eluting with ethyl acetate/hexane (1:4), yielded the title compound as a colourless oil.

Workup

  1. customAfter 20 min the cold bath was removed
  2. customquenched with a saturated solution of ammonium chloride
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customPurification by column chromatography
  9. washeluting with ethyl acetate/hexane (1:4)

Sources & evidence

ORD record
ord-27d79bba010c479c936a965ddb4a889c
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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