Solketal → 2,2-Dimethyl-1,3-dioxolan-4-ylmethyl [2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetate

HRID 1200192Notes

Reaction equation

HRID 1200192 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.[CH3:22][C:23]1([CH3:30])[O:27][CH:26]([CH2:28]O)[CH2:25][O:24]1.C1(N=C=NC2CCCCC2)CCCCC1>ClCCl>[C:1]1([C:7]2[O:8][C:9]3[C:17]([CH2:18][C:19]([O:21][CH2:28][CH:26]4[CH2:25][O:24][C:23]([CH3:30])([CH3:22])[O:27]4)=[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

5

Reactant 3

HCID 7528SolketalHCID 10868DicyclohexylcarbodiimideHCID 14650449HCID 14650449, compound

Product 1

HCID 536602762,2-Dimethyl-1,3-dioxolan-4-ylmethyl [2-(1-cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetateYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[2-(1-Cyclohexenyl)-4-oxo-4H-[1]-benzopyran-8-yl]acetic acid (2.84 g), 2,2-dimethyl-1,3-dioxolan-4-methanol (3.96 g) and dicyclohexylcarbodiimide (2.28 g) were added to dichloromethane (30 ml) with ice cooling and then the mixture was stirred at room temperature for 18 hours. The mixture was concentrated under reduced pressure and the residue was purified by silica gel column chromatography to obtain the title compound (2.65 g), yield 67%, m.p. 104°-105° C. (recrystallized from ethyl acetate).

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography
  3. customto obtain
  4. customthe title compound (2.65 g), yield 67%, m.p. 104°-105° C. (recrystallized from ethyl acetate)

Sources & evidence

ORD record
ord-313761d85bee4237925d88cd454d8320
Source dataset
uspto-grants-1990_02
Patent number
US04904690

Reaction notes

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