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Dimethylformamide → t-Butyl [[6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetate

HRID 652666
ノート
印刷プレビュー

反応式

HRID 652666 の反応式
[Cl:1][C:2]1[C:3]([OH:16])=[CH:4][C:5]2[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[OH:11])[S:7][C:6]=2[C:14]=1[Cl:15].Br[CH2:18][C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>CC(=O)CC>[C:22]([O:21][C:19](=[O:20])[CH2:18][O:16][C:3]1[C:2]([Cl:1])=[C:14]([Cl:15])[C:6]2[S:7][C:8]([C:10]([OH:11])([CH3:13])[CH3:12])=[CH:9][C:5]=2[CH:4]=1)([CH3:25])([CH3:24])[CH3:23]
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 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 79177tert-Butyl bromoacetateHCID 132900426,7-Dichloro-5-hydroxy-alpha,alpha-dimethylbenzo[b]thiophene-2-methanol

生成物 1

HCID 13290043t-Butyl [[6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetate

試薬・触媒・溶媒 1

HCID 6569
Methyl Ethyl Ketone
溶媒
2 回

実験手順

To a mixture of 6,7-dichloro-5-hydroxy-α,α-dimethylbenzo[b]thiophene-2-methanol in 250 ml of 2-butanone is added a solution of 7.7 g of t-butyl bromoacetate in 50 ml 2-butanone and the resultant mixture is placed in a preheated oil-bath at 95°. To the mixture is added 6.7 g of potassium carbonate and 3 ml of dimethylformamide and the reaction mixture is refluxed at 95° for 21/2 hrs. The cooled mixture is filtered and 100 ml of water is added. The layers are separated and the aqueous phase is extracted two times with ethyl ether. The organic extracts are washed, dried over anhydrous magnesium sulfate, filtered and concentrated to give a solid. Recrystallization from ethyl ether and pentane gives 11.5 g of t-butyl[[6,7-dichloro-2-(1-hydroxy-1-methylethyl)benzo[b]thien-5-yl]oxy]acetate, mp 137°-138°.

後処理

  1. temperaturethe reaction mixture is refluxed at 95° for 21/2 hrs
  2. filtrationThe cooled mixture is filtered
  3. addition100 ml of water is added
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted two times with ethyl ether
  6. washThe organic extracts are washed
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a solid
  11. customRecrystallization from ethyl ether and pentane

出典と根拠

ORDレコード
ord-e86b63f8a4604af68e0db4e831f2d061
出典データセット
uspto-grants-1987_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04672138

反応ノート

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