Water → HCID 13648318, compound

HRID 1982349Notes

Reaction equation

HRID 1982349 reaction equation
[OH:1][C:2]1[CH:18]=[CH:17][C:5]([O:6][CH:7]([CH3:16])[C:8]([O:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])=[O:9])=[CH:4][CH:3]=1.[OH-].[Ca+2].[OH-].Cl[C:23]1[O:24][C:25]2[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:26]=2[N:27]=1.O>CS(C)=O>[Cl:32][C:30]1[CH:29]=[CH:28][C:26]2[N:27]=[C:23]([O:1][C:2]3[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH3:16])[C:8]([O:10][CH2:11][Si:12]([CH3:14])([CH3:13])[CH3:15])=[O:9])=[CH:17][CH:18]=3)[O:24][C:25]=2[CH:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 771752,6-DichlorobenzoxazoleHCID 6093208Calcium HydroxideHCID 13648314HCID 13648314, compound

Product 1

HCID 13648318HCID 13648318, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of 6.7 g (0.025 mole) of the R-enantiomer of trimethylsilyl-methyl 2-(4-hydroxy-phenoxy)-propionate, 0.9 g of calcium hydroxide and 10 ml of dimethylsulphoxide is heated at 40° C. A solution of 4.7 g (0.025 mole) of 2,6-dichlorobenzoxazole in 15 ml of dimethylsulphoxide is slowly added dropwise at this temperature, with stirring. The reaction mixture is subsequently stirred at 40° C. for 2 hours and at room temperature for 16 hours. Working up is then carried out by pouring the reaction mixture into water, extracting the resulting oily product with cyclohexane, washing the organic phase successively with dilute aqueous sodium hydroxide solution and water, rendering it weakly acidic with glacial acetic acid and then drying it and concentrating it under reduced pressure. 9.3 g (88.6% of theory) of the R-enantiomer of trimethylsilyl-methyl 2-{4-[(6-chloro-2-benzoxazolyl)-oxy]-phenoxy}-propionate are obtained in this manner in the form of crystals.

Workup

  1. stirringThe reaction mixture is subsequently stirred at 40° C. for 2 hours and at room temperature for 16 hours
  2. extractionextracting the resulting oily product with cyclohexane
  3. washwashing the organic phase successively with dilute aqueous sodium hydroxide solution and water
  4. customdrying it
  5. concentrationconcentrating it under reduced pressure

Sources & evidence

ORD record
ord-0c1afe8d0e1544659abaca7241adc74b
Source dataset
uspto-grants-1986_06
Patent number
US04596594

Reaction notes

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