Dichloromethane → HCID 19352726, compound

HRID 725680Notes

Reaction equation

HRID 725680 reaction equation
[CH2:1]([O:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH:27]([OH:29])[CH3:28])=[CH:18][CH:17]=2)=[N:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(N(CC)CC)C.ClCCl.[C:40](Cl)(=[O:43])[CH2:41][CH3:42]>C(Cl)(Cl)Cl>[CH2:1]([O:9][C:10]1[CH:15]=[N:14][C:13]([C:16]2[CH:17]=[CH:18][C:19](/[CH:22]=[CH:23]/[CH2:24][CH2:25][CH2:26][CH:27]([O:29][C:40](=[O:43])[CH2:41][CH3:42])[CH3:28])=[CH:20][CH:21]=2)=[N:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 19352687HCID 19352687, compound

Product 1

HCID 19352726HCID 19352726, compoundYield 88.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A reactor was charged with 1.6 g (4 mmol) of the (-)-5-octyloxy-2-{4-(6-hydroxy-heptyl)-phenyl}-pyrimidine obtained in Example 9, 2 g of triethylamine and 30 g of dichloromethane, to which was dropwise added 0.6 g (6 mmol) of propionyl chloride at a temperature not exceeding 10° C. The mixture was reacted first at 0°-10° C. for one hour and thereafter at 20°-30° C. for 2 hours. After the reaction, the reaction mixture was poured into ice water, and the mixture thus obtained was separated into two phases. The organic layer was washed successively with 5% hydrochloric acid, water, 5% aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride, dried over magnesium sulfate, and concentrated under reduced pressure. Purification of the residue by silica gel column chromatography gave 1.6 g (yield 85%) of (+)-5-octyloxy-2-{4-(6-propionyloxy-1-trans-heptenyl)-phenyl}-pyrimidine, [α]D20 =+0.96 (c=1.1, CHCl3).

Workup

  1. customexceeding 10° C
  2. customThe mixture was reacted first at 0°-10° C. for one hour
  3. customAfter the reaction
  4. customthe mixture thus obtained
  5. customwas separated into two phases
  6. washThe organic layer was washed successively with 5% hydrochloric acid, water, 5% aqueous solution of sodium bicarbonate and saturated aqueous solution of sodium chloride
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customPurification of the residue by silica gel column chromatography

Sources & evidence

ORD record
ord-218fbaac249d45578429fa9c119c973e
Source dataset
uspto-grants-1998_01
Patent number
US05707547

Reaction notes

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