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Ammonium Chloride → 1-(1,3-Benzodioxol-5-yl)-3-(1,3-dioxol-2-yl)-1-propanone

HRID 486527
ノート
印刷プレビュー

反応式

HRID 486527 の反応式
Br[CH2:2][CH2:3][CH:4]1[O:8][CH2:7][CH2:6][O:5]1.[Mg].[Cl-].[Mg+2].[Cl-].CON(C)[C:16]([C:18]1[CH:26]=[CH:25][C:21]2[O:22][CH2:23][O:24][C:20]=2[CH:19]=1)=[O:17].[Cl-].[NH4+]>O1CCCC1.O>[O:22]1[C:21]2[CH:25]=[CH:26][C:18]([C:16](=[O:17])[CH2:2][CH2:3][CH:4]3[O:8][CH:7]=[CH:6][O:5]3)=[CH:19][C:20]=2[O:24][CH2:23]1
参加物実験手順後処理出典と根拠反応ノート

参加物

8

反応物 5

HCID 25517Ammonium ChlorideHCID 877762-(2-Bromoethyl)-1,3-dioxolaneHCID 5360315Magnesium ChlorideHCID 5462224MagnesiumHCID 10921728N-methoxy-N-methylbenzo[d][1,3]dioxole-5-carboxamide

生成物 1

HCID 190952701-(1,3-Benzodioxol-5-yl)-3-(1,3-dioxol-2-yl)-1-propanone収率 72%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

2-(2-Bromoethyl)-1,3-dioxolane (4.5 ml) was added dropwise within 15 minutes under argon and while stirring at a maximum 30° C. to a suspension of Rieke magnesium, prepared from 5.1 g of magnesium chloride, in 150 ml of absolute tetrahydrofuran. The suspension was stirred at room temperature for 30 minutes, cooled to -70° C. and treated within 10 minutes with 6.1 g of N-methoxy-N-methyl-1,3-benzodioxol-5-carboxamide. The reaction mixture was stirred at -70° C. for 30 minutes and at room temperature for 2 hours and subsequently hydrolyzed with 100 ml of saturated ammonium chloride solution while cooling at a maximum 20° C. After the addition of 50 ml of water the mixture was extracted once with 150 ml of ethyl acetate and twice with 100 ml of ethyl acetate each time. The combined organic extracts were dried over MgSO4 and freed from solvent. The residue, 8.0 g of yellow oil, was chromatographed on 490 g of silica gel with ethyl acetate/hexane (1:5) as the eluent. 5.3 g (72%) of 1-(1,3-benzodioxol-5-yl)-3-(1,3-dioxol-2-yl)-1-propanone were isolated as a colourless solid. A sample crystallized colourless from a 20-fold amount of diethyl ether and melted at 94°-96° C.

後処理

  1. temperaturecooled to -70° C.
  2. temperaturewhile cooling at a maximum 20° C
  3. extractionwas extracted once with 150 ml of ethyl acetate and twice with 100 ml of ethyl acetate each time
  4. dry with materialThe combined organic extracts were dried over MgSO4
  5. customThe residue, 8.0 g of yellow oil, was chromatographed on 490 g of silica gel with ethyl acetate/hexane (1:5) as the eluent

出典と根拠

ORDレコード
ord-7ae7d278f1024e268d3e07302079e164
出典データセット
uspto-grants-1994_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05292732

反応ノート

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