Ammonia → Muskone

HRID 1885760ノート

反応式

HRID 1885760 の反応式
[C:1]1(=[O:16])[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.N.[Cl-].[NH4+].[CH2:20](OCC)C>>[CH3:20][CH:14]1[CH2:15][C:1](=[O:16])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

参加物

5

反応物 4

HCID 222AmmoniaHCID 3283Diethyl EtherHCID 25517Ammonium ChlorideHCID 11074987(2E)-cyclopentadec-2-en-1-one

生成物 1

HCID 10947Muskone

実験手順

In 10 ml of dried diethyl ether was dissolved 5 mmol of (E)-2-cyclopentadecenone, and the solution was added dropwise to the above solution at -78° C. The mixture was allowed to react at that temperature for 15 hours, and 12 ml of a 1:1 (by volume) mixture of aqueous ammonia and a saturated ammonium chloride aqueous solution was added thereto. The reaction mixture was extracted with diethyl ether, and the extracted product was purified by silica gel column chromatography using hexane/ethyl acetate (45:1 by volume) to obtain muscone in a chemical yield of 57 mol %. The resulting muscone was R-form having an optical rotation of -11.6° (at 21° C., c 5.03, MeOH) and an optical purity of 99%ee.

後処理

  1. additionthe solution was added dropwise to the above solution at -78° C
  2. customto react at that temperature for 15 hours
  3. extractionThe reaction mixture was extracted with diethyl ether
  4. customthe extracted product was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-29b1c5d5feae4e74a836f42eda370643
出典データセット
uspto-grants-1992_09
特許番号
US05146003

反応ノート

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