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

HRID 544435
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인쇄 미리보기

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HRID 544435 반응식
[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([CH3:26])[C@@H:18]([CH:19]=[C:20]([CH3:22])[CH3:21])[C@H:17]1[C:23](Cl)=[O:24].Cl>C1C=CC=CC=1.N1C=CC=CC=1>[CH3:15][C:16]1([CH3:26])[C@@H:18]([CH:19]=[C:20]([CH3:21])[CH3:22])[C@H:17]1[C:23]([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:24]
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참가 물질

6

반응물 3

HCID 313Hydrochloric AcidHCID 12879987(1R,3S)-2,2-dimethyl-3-(2-methylprop-1-en-1-yl)cyclopropane-1-carbonyl chlorideHCID 13106154(2-Phenoxy-5-thiazolyl)-methanol

생성물 1

HCID 56984089(2-phenoxy-5-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-1-carboxylate

시약·촉매·용매 2

HCID 241Benzene용매
HCID 1049
Pyridine
용매

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온도
20 °C

실험 절차

2.07 g of (2-phenoxy-5-thiazolyl)-methanol were added to a solution of (1R,3S) 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane-1-carboxylic acid chloride prepared from 1.68 g of the corresponding acid in 20 ml of benzene and 0.81 ml of pyridine were added dropwise thereto. The mixture was stirred at 20° C. for 17 hours and was poured into dilute aqueous hydrochloric acid. The decanted aqueous phase was extracted with ether and the combined organic phases were washed with water, dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and eluted with an 8-2 cyclohexane-ethyl acetate mixture to obtain 1.6 g of (2-phenoxy-5-thiazolyl)-methyl (1R,3S) 2,2-dimethyl-3-(2-methyl-1-propenyl)-cyclopropane -1-carboxylate.

후처리

  1. additionwere added dropwise
  2. extractionThe decanted aqueous phase was extracted with ether
  3. washthe combined organic phases were washed with water
  4. customdried
  5. customevaporated to dryness under reduced pressure
  6. customThe residue was chromatographed over silica gel
  7. washeluted with an 8-2 cyclohexane-ethyl acetate mixture

출처 및 근거

ORD 기록
ord-e32ba24ffaca476081d2155d6e53b66a
출처 데이터셋
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US04450169

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