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

HRID 544433
ノート
印刷プレビュー

反応式

HRID 544433 の反応式
[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]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 12952597HCID 12952597、化合物HCID 13106154(2-Phenoxy-5-thiazolyl)-methanol

生成物 1

HCID 13102632(2-phenoxy-5-thiazolyl)-methyl (1R,3R) 2,2-dimethyl-3-(cyclopentylidenemethyl)-cyclopropane-1-carboxylate収率 52.7%

試薬・触媒・溶媒 1

HCID 241
Benzene
溶媒

反応条件

温度
20 °C

実験手順

2.74 g of (2-phenoxy-5-thiazolyl)-methanol were added to a solution of 2 g of (1R,3R) 2,2-dimethyl-3-(cyclopentylidenemethyl)-cyclopropane-1-carboxylic acid chloride [described in French Pat. No. 74405 published under No. 1,505,423] in 30 ml of benzene and 0.81 ml of pyridine was added dropwise thereto. The mixture was stirred at 20° C. for 20 hours and was poured into dilute aqueous hydrochloric acid. The decanted aqueous phase was extracted with ether and the combined organic phases were dried and evaporated to dryness under reduced pressure. The residue was chromatographed over silica gel and was eluted with an 8-2 cyclohexane-ethyl acetate mixture to obtain 1.9 g of (2-phenoxy-5-thiazolyl)-methyl (1R,3R) 2,2-dimethyl-3-(cyclopentylidenemethyl)-cyclopropane-1-carboxylate meltingat 67° C.

後処理

  1. extractionThe decanted aqueous phase was extracted with ether
  2. customthe combined organic phases were dried
  3. customevaporated to dryness under reduced pressure
  4. customThe residue was chromatographed over silica gel
  5. washwas eluted with an 8-2 cyclohexane-ethyl acetate mixture

出典と根拠

ORDレコード
ord-cffe2e7ff1fa477baa9dd345ea92d4e2
出典データセット
uspto-grants-1984_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04450169

反応ノート

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