tert-Butyl methyl ether → Benzyl methyl(15-phenylpentadec-5-en-1-yl)carbamate

HRID 1525800노트

반응식

HRID 1525800 반응식
[Br-].C1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)C=CC=CC=1.CC(C)([O-])C.[K+].[CH3:43][N:44]([CH2:55][CH2:56][CH2:57][CH2:58][CH:59]=O)[C:45](=[O:54])[O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1.C(OC)(C)(C)C>O1CCCC1.O>[CH3:43][N:44]([CH2:55][CH2:56][CH2:57][CH2:58][CH:59]=[CH:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)[C:45](=[O:54])[O:46][CH2:47][C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1

참가 물질

7

반응물 4

HCID 15413tert-Butyl methyl etherHCID 23665647Potassium tert-butoxideHCID 86126936Triphenyl(10-phenyldecyl)phosphonium bromideHCID 86722745Benzyl methyl(5-oxopentyl)carbamate

생성물 1

HCID 86722744Benzyl methyl(15-phenylpentadec-5-en-1-yl)carbamate수율 88.1%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Compound 12 (6.5 g) was dissolved in tetrahydrofuran (18 mL). Potassium-tert-butoxide (1.2 g) was added thereto at 0° C., followed by stirring at room temperature for 30 minutes. After cooling the reaction solution to 0° C., the solution of Compound 14 (1.7 g) in tetrahydrofran (3 mL) was added drop wise thereto, followed by the stirring at the same temperature for 2 hours. To the reaction solution, tert-butylmethylether (40 mL) and water (30 mL) were added. The organic layer was washed with water and an aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane:ethylacetate=1:1→1:2) to obtain the title compound (2.7 g) having the following physical property values.

후처리

  1. customat 0° C.
  2. temperatureAfter cooling the reaction solution to 0° C.
  3. customfor 2 hours
  4. washThe organic layer was washed with water
  5. dry with materialan aqueous saturated sodium chloride solution, dried with anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe obtained residue was purified by silica gel column chromatography (hexane:ethylacetate=1:1→1:2)

출처 및 근거

ORD 기록
ord-01c9caffcb56475c99d8520553e32dbe
출처 데이터셋
uspto-grants-2015_07
특허 번호
US09085523B2

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