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

HRID 1525800Notes

Reaction equation

HRID 1525800 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-01c9caffcb56475c99d8520553e32dbe
Source dataset
uspto-grants-2015_07
Patent number
US09085523B2

Reaction notes

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