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Acetic Acid → (R)alpha-methyl-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propynyl]-cyclopropane-carboxylate

HRID 569534
ノート
印刷プレビュー

反応式

HRID 569534 の反応式
[CH3:1][C:2]1([CH3:33])[C@@H:4]([C:5]#[C:6][C:7](=[O:14])[O:8]CC(Cl)(Cl)Cl)[C@H:3]1[C:15]([O:17][C@H:18]([CH3:32])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:20]=1)=[O:16].C(O)(=O)C.O>C(Cl)Cl.[Zn]>[CH3:1][C:2]1([CH3:33])[C@@H:4]([C:5]#[C:6][C:7](=[O:8])[OH:14])[C@H:3]1[C:15]([O:17][C@H:18]([CH3:32])[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:20]=1)=[O:16]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 176Acetic AcidHCID 962WaterHCID 53655047(R)alpha-methyl-3-phenoxy-benzyl (IR,cis) 2,2-dimethyl-3-[3-oxo-3-(2,2,2-trichloroethoxy)-1-propynyl]-cyclopropane-carboxylate

生成物 1

HCID 54097883(R)alpha-methyl-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propynyl]-cyclopropane-carboxylate収率 98.8%

試薬・触媒・溶媒 2

HCID 23994
Zinc
触媒
2 回
HCID 6344Dichloromethane溶媒

実験手順

A solution of 4.16 g of the product of Step A in 4 ml of methylene chloride was admixed with 45 ml of acetic acid containing 10% of water and 0.53 g of zinc powder and the mixture was stirred for 30 minutes at room temperature, then another 0.53 g of zinc powder were added 4 times until The reaction was complete and after 3 hours contact, the mixture was filtered. The filtrate was extracted with methylene chloride and the organic phase was washed with water, dried and evaporated to dryness by azeotropic distillation with toluene to obtain 3.05 g of (R)α-methyl-3-phenoxy-benzyl(1R,cis)2,2-dimethyl-3-[3-oxo-3-hydroxy-1-propynyl]-cyclopropane-carboxylate.

後処理

  1. waitwas complete and after 3 hours
  2. filtrationcontact, the mixture was filtered
  3. extractionThe filtrate was extracted with methylene chloride
  4. washthe organic phase was washed with water
  5. customdried
  6. customevaporated to dryness by azeotropic distillation with toluene

出典と根拠

ORDレコード
ord-b288640e5bc24d34bc9befb20ce292f4
出典データセット
uspto-grants-1988_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04732903

反応ノート

読み込み中…

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