Chlorosuccinimide → HCID 18005866, compound

HRID 989282Notes

Reaction equation

HRID 989282 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[O:9]2)=[CH:4][CH:3]=1.[Cl:17]N1C(=O)CCC1=O>C1COCC1>[Cl:17][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:2]=1[OH:1])[O:9][CH:8]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:7][CH2:6]2

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11085381Ethyl 7-hydroxychromane-2-carboxylate

Product 1

HCID 18005866HCID 18005866, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of ethyl 7-hydroxychroman-2-carboxylate (5.0 g, 22.5 mmol) in THF is treated with N-chlorosuccinimide (NCS) (3.6 g, 27 mmol), stirred for 40 hr and concentrated in vacuo. The resultant residue is purified chromatographically (silica gel/20% EtOAc in hexanes as eluent) to give the title product, 3.0 g (52% yield), identified by NMR and mass spectral analyses.

Workup

  1. concentrationconcentrated in vacuo
  2. customThe resultant residue is purified chromatographically (silica gel/20% EtOAc in hexanes as eluent)

Sources & evidence

ORD record
ord-719dc594dca048ce95a7e05ba4fa700b
Source dataset
uspto-grants-2003_10
Patent number
US06638972B2

Reaction notes

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