Diethyl Ether → 1,3-Diacetoxymethyl-5-[2-[1-(formylmethyl)cyclohexyl]ethoxy]benzene

HRID 2223911ノート

反応式

HRID 2223911 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([O:17][CH2:18][CH2:19][C:20]2([CH2:26][CH2:27][OH:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:9]=[C:10]([CH2:12][O:13][C:14](=[O:16])[CH3:15])[CH:11]=1)(=[O:3])[CH3:2].IC1C=CC=CC=1.C(O)(=O)C.C(O)(=O)C.C(OCC)C>ClCCl>[C:1]([O:4][CH2:5][C:6]1[CH:7]=[C:8]([O:17][CH2:18][CH2:19][C:20]2([CH2:26][CH:27]=[O:28])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]2)[CH:9]=[C:10]([CH2:12][O:13][C:14](=[O:16])[CH3:15])[CH:11]=1)(=[O:3])[CH3:2]

参加物

5

反応物 3

HCID 3283Diethyl EtherHCID 12217721Iodo benzene diacetateHCID 597148422-[1-[2-(3,5-Diacetoxymethylphenyoxy)ethyl]cyclohexyl]ethanol

生成物 1

HCID 597148671,3-Diacetoxymethyl-5-[2-[1-(formylmethyl)cyclohexyl]ethoxy]benzene収率 112%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 2-[1-[2-(3,5-diacetoxymethylphenyoxy)ethyl]cyclohexyl]ethanol (synthesized in Example 31) (430 mg) dissolved in dichloromethane (5 mL) were added diacetic acid iodobenzene (388 mg) and 2,2,6,6-tetramethyl-1-piperidinyloxy free radical (18.5 mg) successively at room temperature. The solution was stirred for 15 hours. Diethyl ether was added to the solution and it was washed in turn with a 10% aqueous sodium thiosulfate solution, 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate, and filtered. The filtrate was then concentrated under reduced pressure to give the title compound (479 mg). This product was subjected to the subsequent step without further purification.

後処理

  1. washwas washed in turn with a 10% aqueous sodium thiosulfate solution, 1N hydrochloric acid, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium chloride solution
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was then concentrated under reduced pressure

出典と根拠

ORDレコード
ord-d53b53f0c2a1433284284812a42b4bcb
出典データセット
uspto-grants-2008_05
特許番号
US07375115B2

反応ノート

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