Hydrochloric Acid → (2-phenoxy-5-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-(cyclopentylidenemethyl)-cyclopropane-1-carboxylate

HRID 544437Notes

Reaction equation

HRID 544437 reaction equation
[O:1]([C:8]1[S:9][C:10]([CH2:13][OH:14])=[CH:11][N:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:15][C:16]1([CH3:28])[C@@H:18]([CH:19]=[C:20]2[CH2:24][CH2:23][CH2:22][CH2:21]2)[C@H:17]1[C:25](Cl)=[O:26].N1C=CC=CC=1.Cl>C1C=CC=CC=1>[CH3:15][C:16]1([CH3:28])[C@@H:18]([CH:19]=[C:20]2[CH2:21][CH2:22][CH2:23][CH2:24]2)[C@H:17]1[C:25]([O:14][CH2:13][C:10]1[S:9][C:8]([O:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[N:12][CH:11]=1)=[O:26]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 13106154(2-Phenoxy-5-thiazolyl)-methanolHCID 45082002(1R,3S)-3-(Cyclopentylidenemethyl)-2,2-dimethylcyclopropane-1-carbonyl chloride

Product 1

HCID 13102631(2-phenoxy-5-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-(cyclopentylidenemethyl)-cyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
20 °C

Procedure

3.1 g of (2-phenoxy-5-thiazolyl)-methanol were added to a solution of (1R,3S) 2,2-dimethyl-3-(cyclopentylidenemethyl)-cyclopropane-1-carboxylic acid chloride prepared from 2.9 g of the corresponding acid [described in French Pat. No. 70-00265 published under No. 2.076.204] in 45 ml of benzene and 1.2 ml of pyridine were added dropwise thereto at 10° C. The mixture was stirred at 20° C. for 17 hours and was poured into dilute aqueous hydrochloric acid solution. The decanted aqueous phasewas extracted with ether and the combined organic phases were washed with water, dried and evaporated to dryness under reduced pressure. The residuewas chromatographed over silica gel and was eluted with a 7-3 hexane-isopropyl ether mixture to obtain 1.3 g of (2-phenoxy-5-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-(cyclopentylidenemethyl)-cyclopropane-1-carboxylate meltingat less than 50° C.

Workup

  1. customat 10° C
  2. extractionThe decanted aqueous phasewas extracted with ether
  3. washthe combined organic phases were washed with water
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customThe residuewas chromatographed over silica gel
  7. washwas eluted with a 7-3 hexane-isopropyl ether mixture

Sources & evidence

ORD record
ord-b10ce3072b19465dbe884281bb1729f5
Source dataset
uspto-grants-1984_05
Patent number
US04450169

Reaction notes

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