Water → 2,2-Dimethylpropyl [2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl)acetate

HRID 1200191Notes

Reaction equation

HRID 1200191 reaction equation
[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([OH:21])=[O:20])=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1.C1N=CN(C(N2C=NC=C2)=O)C=1.[CH3:34][C:35]([CH3:39])([CH3:38])[CH2:36]O.O>CN(C)C=O>[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([O:21][CH2:34][C:35]([CH3:39])([CH3:38])[CH3:36])=[O:20])=[CH:16][CH:15]=[CH:14][C:10]=3[C:11](=[O:13])[CH:12]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6404Neopentyl alcoholHCID 682631,1'-CarbonyldiimidazoleHCID 14650449HCID 14650449, compound

Product 1

HCID 146504632,2-Dimethylpropyl [2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl)acetateYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[2-(1-Cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetic acid (2.84 g) was dissolved in dimethylformamide (30 ml) and carbodiimidazole (1.78 g) was added to the solution. After stirring at room temperature for 2 hours, 2,2-dimethyl-propanol (0.88 g) was added. After stirring at 60° C. for 4 hours, water was added and the mixture was extracted with ethyl acetate. The extracted layer was washed with water, dried and concentrated. The residue was purified by silica gel column chromatography to obtain the title compound (0.82 g), yield 23%, m.p. 138°-139° C. (recrystallized from hexane-ethyl acetate).

Workup

  1. stirringAfter stirring at 60° C. for 4 hours
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extracted layer was washed with water
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography
  7. customto obtain
  8. customthe title compound (0.82 g), yield 23%, m.p. 138°-139° C. (recrystallized from hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c615cf7999374561b39b79dc8b30d5df
Source dataset
uspto-grants-1990_02
Patent number
US04904690

Reaction notes

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