Potassium Carbonate → Diethyl 4-[[[3 (4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]methyl]-1,3 oxathiolane-2,2-dipropanoate

HRID 1383133ノート

反応式

HRID 1383133 の反応式
[CH2:1]([C:4]1[C:14]([OH:15])=[C:13]([C:16](=[O:18])[CH3:17])[CH:12]=[CH:11][C:5]=1[O:6][CH2:7][CH2:8][CH2:9]Br)[CH2:2][CH3:3].[SH:19][CH2:20][CH:21]1[CH2:25][O:24][C:23]([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])[S:22]1.C(=O)([O-])[O-].[K+].[K+]>C(C(C)=O)C>[C:16]([C:13]1[CH:12]=[CH:11][C:5]([O:6][CH2:7][CH2:8][CH2:9][S:19][CH2:20][CH:21]2[CH2:25][O:24][C:23]([CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])([CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[S:22]2)=[C:4]([CH2:1][CH2:2][CH3:3])[C:14]=1[OH:15])(=[O:18])[CH3:17]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27752211-[4-(3-bromopropoxy)-2-hydroxy-3-propylphenyl]ethanoneHCID 14405886Diethyl 4-(mercaptomethyl)-1,3-oxathiolane-2,2-dipropanoate

生成物 1

HCID 14405887Diethyl 4-[[[3 (4-acetyl-3-hydroxy-2-propylphenoxy)propyl]thio]methyl]-1,3 oxathiolane-2,2-dipropanoate収率 96.4%

試薬・触媒・溶媒 1

HCID 6569Methyl Ethyl Ketone溶媒

実験手順

3-(2-n-Propyl-3-hydroxy-4-acetylphenoxy)-1-bromopropane (2.0 g, 0.006 mol), prepared by the method described in U.S. Pat. No. 4,565,882, Example 14, incorporated herein by reference, was dissolved in methyl ethyl ketone (20 ml). To this solution was added the thiol of Example 1 (2.0 g, 0.006 mol) and anhydrous potassium carbonate (2.5 g) and the reaction mixture was refluxed with stirring under a nitrogen atmosphere for 24 hrs. The reaction was cooled to room temperature, filtered and the filtrate concentrated on the rotary evaporator. The residue was chromatographed on silica gel using 25% ethyl acetate/hexane as eluent to give 3.3 g (95%) of the title compound as an oil.

後処理

  1. temperaturethe reaction mixture was refluxed
  2. filtrationfiltered
  3. concentrationthe filtrate concentrated on the rotary evaporator
  4. customThe residue was chromatographed on silica gel using 25% ethyl acetate/hexane as eluent

出典と根拠

ORDレコード
ord-15e0897c7a0e4c90a9db0e79fe4d871b
出典データセット
uspto-grants-1989_02
特許番号
US04808729

反応ノート

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