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

HRID 1525800ノート

反応式

HRID 1525800 の反応式
[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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-01c9caffcb56475c99d8520553e32dbe
出典データセット
uspto-grants-2015_07
特許番号
US09085523B2

反応ノート

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