Chlorosuccinimide → HCID 131734531, compound

HRID 591535Notes

Reaction equation

HRID 591535 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([OH:14])=[CH:13][C:8]=2[O:7][CH2:6]1.[Cl:16]N1C(=O)CCC1=O>C1COCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][C@H:5]1[C:9]2[CH:10]=[C:11]([Cl:16])[C:12]([OH:14])=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 53393313(S)-Methyl 2-(6-hydroxy-2,3-dihydrobenzofuran-3-yl)acetate

Product 1

HCID 131734531HCID 131734531, compoundYield 86.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of methyl((3S)-6-hydroxy-2,3-dihydro-1-benzofuran-3-yl)acetate (10 g) in THF (dry) (192 mL) was added N-chlorosuccinimide (6.41 g) portionwise at 0° C. The mixture was stirred at room temperature over weekend. The mixture was quenched with water and extracted with EtOAc. The combined organic layer was washed with brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexane) to give the title compound (10.12 g).

Workup

  1. customThe mixture was quenched with water
  2. extractionextracted with EtOAc
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography (EtOAc/hexane)

Sources & evidence

ORD record
ord-c9f1c5622b4b407eb7d7d85b9d9b2520
Source dataset
uspto-grants-2016_01
Patent number
US09238639B2

Reaction notes

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