Acetic Acid → HCID 18410348, compound

HRID 993352Notes

Reaction equation

HRID 993352 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[OH:12])[O:8][C:7](=[O:13])[CH:6]=[C:5]2[CH2:14]Cl.C1C=CC=CC=1.N12CCCN=C1CCCCC2.[C:33]([OH:36])(=[O:35])[CH3:34]>C(Cl)(Cl)Cl>[C:33]([O:36][CH2:14][C:5]1[C:4]2[C:9](=[CH:10][C:11]([OH:12])=[C:2]([Br:1])[CH:3]=2)[O:8][C:7](=[O:13])[CH:6]=1)(=[O:35])[CH3:34]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 241BenzeneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 184103446-Bromo-4-(chloromethyl)-7-hydroxy-2H-1-benzopyran-2-one

Product 1

HCID 18410348HCID 18410348, compoundYield 59.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 67.1 mg (0.232 mmol) of compound 11, dry benzene (2 mL), 175 mL (0.927 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene, and 40 mL (0.70 mmol) of acetic acid was refluxed for 1.5 hours. The reaction mixture was allowed to cool to room temperature, diluted with chloroform (10 mL), quenched with 1N HCl (1 mL) and separated. The organic layer was dried over MgSO4 and evaporated to yield the crude product. Purification by column chromatography (10 g of SiO2, 4.7% methanol-chloroform) gave 43.1 mg (0.138 mmol, 59.4% yield) of compound 5 as an oil. 1H NMR (CDCl3+5% CD3OD) δ 7.56 (1H, s), 6.80 (1H, s), 6.21 (1H, s), 5.14 (2H, s), 2.11 (3H, s); MS (ES, negative) 311.0 and 313.1; UV (KMOPS, pH 7.2) λmax (ε) 370 nm (15,000 M−1cm−1).

Workup

  1. temperaturewas refluxed for 1.5 hours
  2. customquenched with 1N HCl (1 mL)
  3. customseparated
  4. dry with materialThe organic layer was dried over MgSO4
  5. customevaporated
  6. customto yield the crude product
  7. customPurification by column chromatography (10 g of SiO2, 4.7% methanol-chloroform)

Sources & evidence

ORD record
ord-328f548af86f49508c16456b44154afe
Source dataset
uspto-grants-2002_10
Patent number
US06472541B2

Reaction notes

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