Water → Ethyl (2E)-(6-chlorospiro[chromene-2,1'-cyclobutan]-4(3H)-ylidene)acetate

HRID 453925Notes

Reaction equation

HRID 453925 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[O:13][C:9]1([CH2:12][CH2:11][CH2:10]1)[CH2:8][C:7]2=O.[OH2:18]>O1CCCC1.CO>[Cl:3][C:4]1[CH:5]=[C:6]2[C:14](=[CH:15][CH:16]=1)[O:13][C:9]1([CH2:12][CH2:11][CH2:10]1)[CH2:8]/[C:7]/2=[CH:8]\[C:9]([O:13][CH2:14][CH3:6])=[O:18]

Participants

6

Reactant 3

HCID 962WaterHCID 24758Sodium hydrideHCID 667465206-Chlorospiro[chroman-2,1'-cyclobutan]-4-one

Product 1

HCID 86652760Ethyl (2E)-(6-chlorospiro[chromene-2,1'-cyclobutan]-4(3H)-ylidene)acetate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

Triethyl phosphonoacetate (4.03 g, 17.897 mmol) was added over 15 min to a stirred and cooled mixture of sodium hydride (431 mg, 17.897 mmol) in anhydrous tetrahydrofuran (25 ml). The reaction mixture was stirred for 30 min and then added 6-Chlorospiro[chromene-2,1′-cyclobutan]-4(3H)-one (2 g, 8.948 mmol) in anhydrous tetrahydrofuran. The reaction mixture was stirred at the same temperature under nitrogen for 24 h. The reaction mixture was diluted with methanol and water and the product was extracted into ethyl acetate (3×100 ml). The organic layer was washed with water (100 ml), brine, dried (Na2SO4) and concentrated to give 3.54 g of the crude product which was used as such for the next step.

Workup

  1. temperaturecooled
  2. stirringThe reaction mixture was stirred for 30 min
  3. stirringThe reaction mixture was stirred at the same temperature under nitrogen for 24 h
  4. extractionthe product was extracted into ethyl acetate (3×100 ml)
  5. washThe organic layer was washed with water (100 ml), brine
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-9865dde7f1a7430eb962b81909d29e7e
Source dataset
uspto-grants-2013_07
Patent number
US08492568B2

Reaction notes

Loading…