Ammonia → Muskone

HRID 1885760

반응식

HRID 1885760 반응식
[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

참가 물질

5

반응물 4

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

생성물 1

HCID 10947Muskone

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-29b1c5d5feae4e74a836f42eda370643
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05146003

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